Fungicide hydroximoyl-tetrazole derivatives

ABSTRACT

The present invention relates to hydroximoyl-tetrazole derivatives of formula (I), their process of preparation, their use as fungicide active agents, particularly in the form of fungicide compositions and methods for the control of phytopathogenic fungi, notably of plants, using these compounds or compositions 
                         
wherein A represents a tetrazoyl group, Het represents a pyridyl group or a thiazolyl group and X represents various substituents.

CROSS-REFERENCE TO RELATED APPLICATION(S)

The present application is a 35 U.S.C. §371 national phase conversion ofPCT/EP2009/058427 filed Jul. 3, 2009, which claims priority of EuropeanApplication No. 08356101.9 filed Jul. 4, 2008. The PCT InternationalApplication was published in the English language.

The present invention relates to hydroximoyl-tetrazole derivatives,their process of preparation, their use as fungicide active agents,particularly in the form of fungicide compositions and methods for thecontrol of phytopathogenic fungi, notably of plants, using thesecompounds or compositions.

In European patent application n^(o) 1426371, there are disclosedcertain tetrazoyloxime derivatives of the following chemical structure:

wherein A represents a tetrazolyl group, Het represents either aparticular pyridinyl group or a particular thiazolyl group.

In Japanese patent application n^(o) 2004-131392, there are disclosedcertain tetrazoyloxime derivatives of the following chemical structure:

wherein Q can be selected in a list of 15 various heterocycle groups.

In Japanese patent application n^(o) 2004-131416, there are disclosedcertain tetrazoyloxime derivatives of the following chemical structure:

wherein Q can be selected among a pyridinyl group or a thiazolyl group.

The compounds disclosed in these three documents do not prove to providea comparable utility than the compounds according to the invention.

It is always of high-interest in agriculture to use novel pesticidecompounds in order to avoid or to control the development of resistantstrains to the active ingredients. It is also of high-interest to usenovel compounds being more active than those already known, with the aimof decreasing the amounts of active compound to be used, whilst at thesame time maintaining effectiveness at least equivalent to the alreadyknown compounds. We have now found a new family of compounds whichpossess the above mentioned effects or advantages.

Accordingly, the present invention provides a tetrazoyloxime derivativeof formula (I)

wherein

-   -   X represents a hydrogen atom, a halogen atom, C₁-C₈-alkyl,        C₁-C₈-alkoxy, a cyano group, a methanesulfonyl group, a nitro        group, a trifluoromethyl group or an aryl group;    -   A represents a tetrazoyl group of formula (A¹) or (A²):

-   -   wherein Y represents substituted or non-substituted C₁-C₈-alkyl;        and    -   Het represents a pyridyl group of formula (Het¹) or a thiazolyl        group of formula (Het²);

-   -   wherein        -   Q represents a substituted or non-substituted            tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl, substituted or            non-substituted tri(C₁-C₈-alkyl)silyl-C₃-C₈-cycloalkyl,            substituted or non-substituted aryl-cyclopropyl, substituted            or non-substituted C₃-C₈-halogenocycloalkyl having 1 to 5            halogen atoms, substituted or non-substituted            C₃-C₈-cycloalkyl-C₁-C₈-alkyl, substituted or non-substituted            C₃-C₈-cycloalkenyl, substituted or non-substituted            C₃-C₈-cycloalkenyl-C₁-C₈-alkyl, a substituted or            non-substituted C₂-C₈-halogenoalkenyl having 1 to 5 halogen            atoms, substituted or non-substituted C₂-C₈-alkynyl,            substituted or non-substituted C₁-C₈-halogenoalkoxy having 1            to 5 halogen atoms, substituted or non-substituted            C₁-C₈-halogenoalkoxyalkyl having 1 to 5 halogen atoms,            substituted or non-substituted phenoxyalkyl, substituted or            non-substituted C₂-C₈-alkenyloxy, substituted or            non-substituted C₂-C₈-halogenoalkenyloxy having 1 to 5            halogen atoms, substituted or non-substituted            C₃-C₈-alkynyloxy, substituted or non-substituted            C₃-C₈-halogenoalkynyloxy having 1 to 5 halogen atoms,            substituted or non-substituted            (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl, substituted or            non-substituted (C₁-C₈-alkenyloxyimino)-C₁-C₈-alkyl,            substituted or non-substituted            (C₁-C₈-alkynyloxyimino)-C₁-C₈-alkyl, substituted or            non-substituted (benzyloxyimino)-C₁-C₈-alkyl, substituted            benzyloxy, substituted or non-substituted phenoxy,            substituted aryl, substituted or non-substituted, saturated            or unsaturated 4-, 5-, 6- or 7-membered heterocyclyl            comprising up to 4 heteroatoms selected in the list            consisting of N, O, S; [substituted aryl]-[C₁-C₈]-alkyl;            substituted or non-substituted, saturated or unsaturated 4-,            5-, 6- or 7-membered heterocyclyl-[C₁-C₈]-alkyl comprising            up to 4 heteroatoms selected in the list consisting of N, O,            S; saturated or unsaturated 4-, 5-, 6- or 7-membered            heterocyclyl-[C₁-C₈]-halogenoalkyl comprising up to 4            heteroatoms selected in the list consisting of N, O, S and            having 1 to 5 halogen atoms; substituted or non-substituted            tri(C₁-C₈-alkyl)-silyloxy, substituted or non-substituted            C₅-C₁₂-fused bicycloalkyl, substituted or non-substituted            C₅-C₁₂-fused bicycloalkenyl, substituted or non-substituted            C₅-C₁₂-fused bicycloalkyl-[C₁-C₈]-alkyl, substituted or            non-substituted C₅-C₁₂-fused bicycloalkenyl-[C₁-C₈]-alkyl,            substituted or non-substituted arylcarbonyl, substituted or            non-substituted C₁-C₈-alkylcarbonyl, substituted or            non-substituted, saturated or unsaturated 4-, 5-, 6- or            7-membered heterocyclylcarbonyl comprising up to 4            heteroatoms selected in the list consisting of N, O, S;            as well as salts, N-oxides, metallic complexes and            metalloidic complexes thereof or (E) and (Z) isomers and            mixtures thereof.

Any of the compounds according to the invention can exist as one or morestereoisomers depending on the number of stereogenic units (as definedby the IUPAC rules) in the compound. The invention thus relates equallyto all the stereoisomers, and to the mixtures of all the possiblestereoisomers, in all proportions. The stereoisomers can be separatedaccording to the methods which are known per se by the man ordinaryskilled in the art.

Notably, the stereostructure of the oxime moiety present in theheterocyclyloxime derivative of formula (I) includes (E) or (Z) isomer,and these stereoisomers form part of the present invention.

According to the invention, the following generic terms are generallyused with the following meanings:

-   -   halogen means fluorine, chlorine, bromine or iodine;    -   heteroatom can be nitrogen, oxygen or sulphur;    -   unless indicated otherwise, a group or a substituent that is        substituted according to the invention can be substituted by one        or more of the following groups or atoms: a halogen atom, a        nitro group, a hydroxy group, a cyano group, an amino group, a        sulphenyl group, a pentafluoro-λ⁶-sulphenyl group, a formyl        group, a substituted or non-substituted carbaldehyde        O—(C₁-C₈-alkyl)oxime, a formyloxy group, a formylamino group, a        carbamoyl group, a N-hydroxycarbamoyl group, a formylamino        group, a (hydroxyimino)-C₁-C₈-alkyl group, a C₁-C₈-alkyl, a        tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl, C₁-C₈-cycloalkyl,        tri(C₁-C₈-alkyl)silyl-C₁-C₈-cycloalkyl, a C₁-C₈-halogenoalkyl        having 1 to 5 halogen atoms, a C₁-C₈-halogenocycloalkyl having 1        to 5 halogen atoms, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, a        C₂-C₈-alkenyloxy, a C₂-C₈-alkynyloxy, a C₁-C₈-alkylamino, a        di-C₁-C₈-alkylamino, a C₁-C₈-alkoxy, a C₁-C₈-halogenoalkoxy        having 1 to 5 halogen atoms, a C₁-C₈-alkylsulphenyl, a        C₁-C₈-halogenoalkylsulphenyl having 1 to 5 halogen atoms, a        C₂-C₈-alkenyloxy, a C₂-C₈-halogenoalkenyloxy having 1 to 5        halogen atoms, a C₃-C₈-alkynyloxy, a C₃-C₈-halogenoalkynyloxy        having 1 to 5 halogen atoms, a C₁-C₈-alkylcarbonyl, a        C₁-C₈-halogenoalkylcarbonyl having 1 to 5 halogen atoms, a        C₁-C₈-alkylcarbamoyl, a di-C₁-C₈-alkylcarbamoyl, a        N—C₁-C₈-alkyloxycarbamoyl, a C₁-C₈-alkoxycarbamoyl, a        N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, a C₁-C₈-alkoxycarbonyl, a        C₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a        C₁-C₈-alkylcarbonyloxy, a C₁-C₈-halogenoalkylcarbonyloxy having        1 to 5 halogen atoms, a C₁-C₈-alkylcarbonylamino, a        C₁-C₈-halogenoalkylcarbonylamino having 1 to 5 halogen atoms,        substituted or non-substituted C₁-C₈-alkoxycarbonylamino,        substituted or non-substituted C₁-C₈-halogenoalkoxycarbonylamino        having 1 to 5 halogen atoms, a C₁-C₈-alkylaminocarbonyloxy, a        di-C₁-C₈-alkylaminocarbonyloxy, a C₁-C₈-alkyloxycarbonyloxy, a        C₁-C₈-alkylsulphenyl, a C₁-C₈-halogenoalkylsulphenyl having 1 to        5 halogen atoms, a C₁-C₈-alkylsulphinyl, a        C₁-C₈-halogenoalkylsulphinyl having 1 to 5 halogen atoms, a        C₁-C₈-alkylsulphonyl, a C₁-C₈-halogenoalkylsulphonyl having 1 to        5 halogen atoms, a C₁-C₈-alkylaminosulfamoyl, a        di-C₁-C₈-alkylaminosulfamoyl, a (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl,        a (C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl, a        (C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl,        (benzyloxyimino)-C₁-C₆-alkyl, C₁-C₈-alkoxyalkyl,        C₁-C₈-halogenoalkoxyalkyl having 1 to 5 halogen atoms,        benzyloxy, benzylsulphenyl, benzylamino, phenoxy,        phenylsulphenyl, or phenylamino;    -   the term “aryl” means phenyl or naphthyl;    -   the term “heterocyclyl” means saturated or unsaturated 4-, 5-,        6- or 7-membered ring comprising up to 4 heteroatoms selected in        the list consisting of N, O, S.

Preferred compounds of formula (I) according to the invention are thosewherein X represents a hydrogen atom, a halogen atom, substituted ornon-substituted C₁-C₈-alkyl, a substituted or non-substitutedC₁-C₈-alkoxy, a cyano group, a methanesulfonyl group, a nitro group, atrifluoromethyl group or an aryl group.

Among the halogen atoms represented for X, a chlorine atom or a fluorineatom is particularly preferred. The substituted or non-substitutedC₁-C₈-alkyl group represented for X is preferably an alkyl group having1 to 4 carbon atoms and specific examples thereof include a methylgroup, an ethyl group, an n-propyl group, an isopropyl group, an n-butylgroup, an isobutyl group, a sec-butyl group, and a tert-butyl group.Among these alkyl groups, a methyl group or a tert-butyl group isparticularly preferred.

The alkoxy group for X is preferably a substituted or non-substitutedC₁-C₈-alkoxy group having 1 to 3 carbon atoms and specific examplesthereof include a methoxy group, an ethoxy group, a propoxy group, andan isopropoxy group. Among these alkoxy groups, a methoxy group or anethoxy group is particularly preferred.

Even more preferred compounds of formula (I) according to the inventionare those wherein X represents a hydrogen atom.

Other preferred compounds of formula (I) according to the invention arethose wherein Y represents a substituted or non-substituted C₁-C₈-alkylgroup. Among these alkyl groups, an alkyl group having 1 to 3 carbonatoms such as a methyl group, an ethyl group, an n-propyl group or anisopropyl group is preferable. Among these alkyl groups, a methyl groupis particularly preferred.

Other preferred compounds of formula (I) according to the invention arethose wherein Q represents a substituted or non-substitutedC₃-C₈-cycloalkyl-C₁-C₈-alkyl, substituted or non-substitutedC₃-C₈-cycloalkenyl, substituted or non-substituted C₂-C₈-alkynyl,substituted or non-substituted C₁-C₈-halogenoalkoxy having 1 to 5halogen atoms, substituted or non-substituted C₁-C₈-halogenoalkoxyalkylhaving 1 to 5 halogen atoms, substituted or non-substitutedphenoxyalkyl, substituted or non-substituted C₂-C₈-alkenyloxy,substituted or non-substituted C₂-C₈-halogenoalkenyloxy having 1 to 5halogen atoms, substituted or non-substituted C₃-C₈-alkynyloxy,substituted or non-substituted C₃-C₈-halogenoalkynyloxy having 1 to 5halogen atoms, substituted benzyloxy, substituted or non-substitutedphenoxy, substituted aryl, substituted or non-substituted, saturated orunsaturated 4-, 5-, 6- or 7-membered heterocyclyl comprising up to 4heteroatoms selected in the list consisting of N, O, S; substituted ornon-substituted, saturated or unsaturated 4-, 5-, 6- or 7-memberedheterocyclyl-[C₁-C₈]-alkyl comprising up to 4 heteroatoms selected inthe list consisting of N, O, S; saturated or unsaturated 4-, 5-, 6- or7-membered heterocyclyl-[C₁-C₈]-halogenoalkyl comprising up to 4heteroatoms selected in the list consisting of N, O, S and having 1 to 5halogen atoms; substituted or non-substituted C₅-C₁₂-fused bicycloalkyl,substituted or non-substituted C₅-C₁₂-fused bicycloalkenyl.

More preferred compounds of formula (I) according to the invention arethose wherein Q represents a substituted or non-substitutedC₃-C₈-cycloalkyl-C₁-C₈-alkyl, substituted or non-substitutedC₃-C₈-cycloalkenyl, substituted or non-substituted C₂-C₈-alkynyl,substituted or non-substituted C₁-C₈-halogenoalkoxy having 1 to 5halogen atoms, substituted or non-substituted phenoxyalkyl, substitutedor non-substituted C₂-C₈-alkenyloxy, substituted or non-substitutedC₃-C₈-alkynyloxy, substituted or non-substitutedC₃-C₈-halogenoalkynyloxy having 1 to 5 halogen atoms, substitutedbenzyloxy, substituted or non-substituted phenoxy, substituted aryl,substituted or non-substituted, saturated or unsaturated 4-, 5-, 6- or7-membered heterocyclyl comprising up to 4 heteroatoms selected in thelist consisting of N, O, S; substituted or non-substituted, saturated orunsaturated 4-, 5-, 6- or 7-membered heterocyclyl-[C₁-C₈]-alkylcomprising up to 4 heteroatoms selected in the list consisting of N, O,S.

Even more preferred compounds of formula (I) according to the inventionare those wherein Q represents a substituted or non-substitutedC₃-C₈-cycloalkyl-C₁-C₈-alkyl, substituted or non-substitutedC₂-C₈-alkynyl, substituted or non-substituted C₁-C₈-halogenoalkoxyhaving 1 to 5 halogen atoms, substituted or non-substitutedphenoxyalkyl, substituted or non-substituted C₂-C₈-alkenyloxy,substituted or non-substituted C₃-C₈-alkynyloxy, substituted aryl,substituted or non-substituted, saturated or unsaturated 4-, 5-, 6- or7-membered heterocyclyl comprising up to 4 heteroatoms selected in thelist consisting of N, O, S; substituted or non-substituted, saturated orunsaturated 4-, 5-, 6- or 7-membered heterocyclyl-[C₁-C₈]-alkylcomprising up to 4 heteroatoms selected in the list consisting of N, O,S

Even more particularly preferred compounds of formula (I) according tothe invention are those wherein Q represents a substituted ornon-substituted C₈-C₈-cycloalkyl-C₁-C₈-alkyl, substituted ornon-substituted C₄-C₈-alkynyl, substituted or non-substitutedC₄-C₈-halogenoalkoxy having 1 to 5 halogen atoms, substituted ornon-substituted phenoxy-[C₁-C₃]-alkyl, substituted or non-substitutedC₄-C₈-alkenyloxy, substituted or non-substituted C₄-C₈-alkynyloxy,substituted aryl, substituted or non-substituted, saturated orunsaturated 4-, 5-, 6- or 7-membered heterocyclyl comprising up to 4heteroatoms selected in the list consisting of N, O, S; substituted ornon-substituted, saturated or unsaturated 4-, 5-, 6- or 7-memberedheterocyclyl-[C₁-C₈]-alkyl comprising up to 4 heteroatoms selected inthe list consisting of N, O, S.

The above mentioned preferences with regard to the substituents of thecompounds of formula (I) according to the invention can be combined invarious manners. These combinations of preferred features thus providesub-classes of compounds according to the invention. Examples of suchsub-classes of preferred compounds according to the invention cancombine:

-   -   preferred features of X with preferred features of one or more        of A¹, A², Y, Het¹, Het² and Q;    -   preferred features of A¹ with preferred features of one or more        of X, A², Y, Het¹, Het² and Q;    -   preferred features of A² with preferred features of one or more        of X, A¹, Y, Het¹, Het² and Q;    -   preferred features of Y with preferred features of one or more        of X, A², A¹, Het¹, Het² and Q;    -   preferred features of Het¹ with preferred features of one or        more of X, A¹, A², Y, Het² and Q;    -   preferred features of Het² with preferred features of one or        more of X, A¹, A², Y, Het¹ and Q;    -   preferred features of Q with preferred features of one or more        of X, A¹, A², Y, Het¹ and Het².

In these combinations of preferred features of the substituents of thecompounds according to the invention, the said preferred features canalso be selected among the more preferred features of each of X, A¹, A²,Y, Het¹, Het² and Q; so as to form most preferred subclasses ofcompounds according to the invention.

The present invention also relates to a process for the preparation ofcompounds of formula (I). Thus, according to a further aspect of thepresent invention, there is a provided process P1 for the preparation ofcompounds of formula (I), as herein-defined, as illustrated by thefollowing reaction scheme:

Process P1

wherein A, X, Z, Q and Het are as herein-defined and LG represents aleaving group. Suitable leaving groups can be selected in the listconsisting of a halogen atom or other customary nucleofugal groups suchas triflate, mesylate or tosylate.

For the compounds of formula (I) according to the invention, there isprovided a second process P2 to yield to a compound of formula (I),according to known methods. In such a case there is provided a processP2 according to the invention and such a process P2 can be illustratedby the following reaction scheme:

Process P2

-   -   wherein A, X, Q are as herein-defined, Het′ represents a pyridyl        group of formula (Het′¹) or a thiazolyl group of formula        (Het′²);

-   -   wherein LG′ represents a leaving group. Suitable leaving groups        can be selected in the list consisting of a halogen atom or        other customary nucleofugal groups such as alcoolate, hydroxide,        carboxylate or cyanide.

For the compounds of formula (Ia), carrying out process P2 wouldpreviously require a deprotection step in order to yield the aminogroup. Amino-protecting groups and related methods of cleavage thereofare known and can be found in T. W. Greene and P. G. M. Wuts, ProtectiveGroup in Organic Chemistry, 3^(rd) ed., John Wiley & Sons.

According to the invention, processes P1 and P2 can be performed ifappropriate in the presence of a solvent and if appropriate in thepresence of a base.

According to the invention, processes P1 and P2 can be performed ifappropriate in the presence of a catalyst. Suitable catalyst can beselected in the list consisting of 4-dimethyl-aminopyridine,1-hydroxy-benzotriazole or dimethylformamide.

In case LG′ represents a hydroxy group, process P2 according to thepresent invention can be performed in the presence of condensing agent.Suitable condensing agent can be selected in the list consisting of acidhalide former, such as phosgene, phosphorous tri-bro-mide, phosphoroustrichloride, phosphorous pentachloride, phosphorous trichloride oxide orthionyl chloride; anhydride former, such as ethyl chloroformate, methylchloroformate, isopropyl chloroformate, isobutyl chloroformate ormethanesulfonyl chloride; carbodiimides, such asN,N′-dicyclohexylcarbodiimide (DCC) or other customary condensingagents, such as phosphorous pentoxide, polyphosphoric acid,N,N′-carbonyl-diimidazole,2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ),triphenylphosphine/tetrachloromethane,4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloridehydrate or bromo-tripyrrolidino-phosphonium-hexafluorophosphate.

Suitable solvents for carrying out processes P1 and P2 according to theinvention are customary inert organic solvents. Preference is given tousing optionally halogenated aliphatic, alicyclic or aromatichydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane,methylcyclohexane, benzene, toluene, xylene or decalin; chlorobenzene,dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride,dichlorethane or trichlorethane; ethers, such as diethyl ether,diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether,dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane oranisole; nitriles, such as acetonitrile, propionitrile, n- oriso-butyronitrile or benzonitrile; amides, such asN,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide,N-methylpyrrolidone or hexamethylphosphoric triamide; esters, such asmethyl acetate or ethyl acetate, sulphoxides, such as dimethylsulphoxide, or sulphones, such as sulpholane.

Suitable bases for carrying out processes P1 and P2 according to theinvention are inorganic and organic bases which are customary for suchreactions. Preference is given to using alkaline earth metal, alkalimetal hydride, alkali metal hydroxides or alkali metal alkoxides, suchas sodium hydroxide, sodium hydride, calcium hydroxide, potassiumhydroxide, potassium tert-butoxide or other ammonium hydroxide, alkalimetal carbonates, such as sodium carbonate, potassium carbonate,potassium bicarbonate, sodium bicarbonate, cesium carbonate, alkalimetal or alkaline earth metal acetates, such as sodium acetate,potassium acetate, calcium acetate, and also tertiary amines, such astrimethylamine, triethylamine, diisopropylethylamine, tributylamine,N,N-dimethylaniline, pyridine, N-methylpiperidine,N,N-dimethyl-aminopyridine, 1,4-diazabicyclo[2.2.2]octane (DABCO),1,5-diazabicyclo[4.3.0]non-5-ene (DBN) or1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

When carrying out processes P1 and P2 according to the invention, thereaction temperature can independently be varied within a relativelywide range.

Generally, process P1 according to the invention is carried out attemperatures between −20° C. and 160° C.

Processes P1 and P2 according to the invention are generallyindependently carried out under atmospheric pressure. However, it isalso possible to operate under elevated or reduced pressure.

When carrying out process P1 according to the invention, generally 1 molor an excess of derivative of formula Het-CH₂-LG and from 1 to 3 mol ofbase are employed per mole of hydroximoyl tetrazole of formula (II). Itis also possible to employ the reaction components in other ratios.

Work-up is carried out by customary methods. Generally, the reactionmixture is treated with water and the organic phase is separated offand, after drying, concentrated under reduced pressure. If appropriate,the remaining residue can be freed by customary methods, such aschromatography or recrystallization, from any impurities that can stillbe present.

Compounds according to the invention can be prepared according to theabove described processes. It will nevertheless be understood that, onthe basis of his general knowledge and of available publications, theskilled worker will be able to adapt these processes according to thespecifics of each of the compounds according to the invention that isdesired to be synthesised.

When A represents a substituent of formula A¹, as herein-described, thecompounds of formula (II), useful as a starting material, can beprepared, for example, by reacting hydroxylamine with the correspondingketones of formula (V)

that can be prepared, for example, according to the method described byR. Raap (Can. J. Chem. 1971, 49, 2139) by addition of a tetrazolyllithium species to esters of formula

or any of their suitable synthetic equivalents like, for example:

When A represents a substituent of formula A², as herein-described, thecompounds of general formula (II) useful as a starting material, can beprepared, for example, from oximes of formula

and 5-substituted tetrazole according to the method described by J.Plenkiewicz et al. (Bull. Soc. Chim. Belg. 1987, 96, 675).

The present invention also relates to a novel process for thepreparation of compounds of formula (I). Thus, according to a furtheraspect of the present invention, there is a provided process P3 for thepreparation of compounds of formula (I), as herein-defined, asillustrated by the following reaction scheme:

Process P3

-   -   wherein A, X, Q are as herein-defined, Het′ represents a pyridyl        group of formula (Het′¹) or a thiazolyl group of formula        (Het′²);

-   -   and LG′ represents a leaving group.

Suitable leaving groups can be selected in the list consisting of ahalogen atom or other customary nucleofugal groups such as alcoolate,hydroxide, carboxylate or cyanide.

The first step of process P3 according to the invention, namely, theconversion of compound of formula (V) into a compound of formula (Ia) iscarried out at temperatures between 110° C. and 180° C.

When carrying out the first step of process P3 according to theinvention, namely, the conversion of compound of formula (V) into acompound of formula (Ia), the reaction is performed under microwaveirradiation.

In a further aspect, the present invention relates to compounds offormula (VI) or one of its salts useful as intermediate compounds ormaterials for the process of preparation P3 according to the invention.The present invention thus provides compounds of formula (VI)

or one of its salts wherein Het′ represents a pyridyl group of formula(Het′¹) or a thiazolyl group of formula (Het′²):

In a further aspect, the present invention also relates to a fungicidecomposition comprising an effective and non-phytotoxic amount of anactive compound of formula (I).

The expression “effective and non-phytotoxic amount” means an amount ofcomposition according to the invention which is sufficient to control ordestroy the fungi present or liable to appear on the crops and whichdoes not entail any appreciable symptom of phytotoxicity for the saidcrops. Such an amount can vary within a wide range depending on thefungus to be controlled, the type of crop, the climatic conditions andthe compounds included in the fungicide composition according to theinvention. This amount can be determined by systematic field trials,which are within the capabilities of a person skilled in the art.

Thus, according to the invention, there is provided a fungicidecomposition comprising, as an active ingredient, an effective amount ofa compound of formula (I) as herein defined and an agriculturallyacceptable support, carrier or filler.

According to the invention, the term “support” denotes a natural orsynthetic organic or inorganic compound with which the active compoundof formula (I) is combined or associated to make it easier to apply,notably to the parts of the plant. This support is thus generally inertand should be agriculturally acceptable. The support can be a solid or aliquid. Examples of suitable supports include clays, natural orsynthetic silicates, silica, resins, waxes, solid fertilizers, water,alcohols, in particular butanol organic solvents, mineral and plant oilsand derivatives thereof. Mixtures of such supports can also be used.

The composition according to the invention can also comprise additionalcomponents. In particular, the composition can further comprise asurfactant. The surfactant can be an emulsifier, a dispersing agent or awetting agent of ionic or non-ionic type or a mixture of suchsurfactants. Mention can be made, for example, of polyacrylic acidsalts, lignosulphonic acid salts, phenolsulphonic ornaphthalenesulphonic acid salts, polycondensates of ethylene oxide withfatty alcohols or with fatty acids or with fatty amines, substitutedphenols (in particular alkylphenols or arylphenols), salts ofsulphosuccinic acid esters, taurine derivatives (in particular alkyltaurates), phosphoric esters of polyoxyethylated alcohols or phenols,fatty acid esters of polyols and derivatives of the above compoundscontaining sulphate, sulphonate and phosphate functions. The presence ofat least one surfactant is generally essential if the active compoundand/or the inert support are water-insoluble and if the vector agent forthe application is water. Preferably, surfactant content can becomprised from 5% to 40% by weight of the composition.

Optionally, additional components can also be included, e.g. protectivecolloids, adhesives, thickeners, thixotropic agents, penetration agents,stabilisers, sequestering agents. More generally, the active compoundscan be combined with any solid or liquid additive, which complies withthe usual formulation techniques.

In general, the composition according to the invention can contain from0.05 to 99% by weight of active compound, preferably 10 to 70% byweight.

Compositions according to the invention can be used in various formssuch as aerosol dispenser, capsule suspension, cold fogging concentrate,dustable powder, emulsifiable concentrate, emulsion oil in water,emulsion water in oil, encapsulated granule, fine granule, flowableconcentrate for seed treatment, gas (under pressure), gas generatingproduct, granule, hot fogging concentrate, macrogranule, microgranule,oil dispersible powder, oil miscible flowable concentrate, oil miscibleliquid, paste, plant rodlet, powder for dry seed treatment, seed coatedwith a pesticide, soluble concentrate, soluble powder, solution for seedtreatment, suspension concentrate (flowable concentrate), ultra lowvolume (ULV) liquid, ultra low volume (ULV) suspension, waterdispersible granules or tablets, water dispersible powder for slurrytreatment, water soluble granules or tablets, water soluble powder forseed treatment and wettable powder. These compositions include not onlycompositions which are ready to be applied to the plant or seed to betreated by means of a suitable device, such as a spraying or dustingdevice, but also concentrated commercial compositions which must bediluted before application to the crop.

The compounds according to the invention can also be mixed with one ormore insecticide, fungicide, bactericide, attractant, acaricide orpheromone active substance or other compounds with biological activity.The mixtures thus obtained have a broadened spectrum of activity. Themixtures with other fungicide compounds are particularly advantageous.The composition according to the invention comprising a mixture of acompound of formula (I) with a bactericide compound can also beparticularly advantageous

According to another object of the present invention, there is provideda method for controlling the phytopathogenic fungi of plants, crops orseeds, characterized in that an agronomically effective andsubstantially non-phytotoxic quantity of a pesticide compositionaccording to the invention is applied as seed treatment, foliarapplication, stem application, drench or drip application (chemigation)to the seed, the plant or to the fruit of the plant or to soil or toinert substrate (e.g. inorganic substrates like sand, rockwool,glasswool; expanded minerals like perlite, vermiculite, zeolite orexpanded clay), Pumice, Pyroclastic materials or stuff, syntheticorganic substrates (e.g. polyurethane) organic substrates (e.g. peat,composts, tree waste products like coir, wood fibre or chips, tree bark)or to a liquid substrate (e.g. floating hydroponic systems, NutrientFilm Technique, Aeroponics) wherein the plant is growing or wherein itis desired to grow.

The expression “are applied to the plants to be treated” is understoodto mean, for the purposes of the present invention, that the pesticidecomposition which is the subject of the invention can be applied bymeans of various methods of treatment such as:

-   -   spraying onto the aerial parts of the said plants a liquid        comprising one of the said compositions,    -   dusting, the incorporation into the soil of granules or powders,        spraying, around the said plants and in the case of trees        injection or daubing,    -   coating or film-coating the seeds of the said plants with the        aid of a plant-protection mixture comprising one of the said        compositions.

The method according to the invention can either be a curing, preventingor eradicating method.

In this method, a composition used can be prepared beforehand by mixingthe two or more active compounds according to the invention.

According to an alternative of such a method, it is also possible toapply simultaneously, successively or separately compounds (A) and (B)so as to have the conjugated (A)/(B) effects, of distinct compositionseach containing one of the two or three active ingredients (A) or (B).

The dose of active compound usually applied in the method of treatmentaccording to the invention is generally and advantageously

-   -   for foliar treatments: from 0.1 to 10,000 g/ha, preferably from        10 to 1,000 g/ha, more preferably from 50 to 300 g/ha; in case        of drench or drip application, the dose can even be reduced,        especially while using inert substrates like rockwool or        perlite;    -   for seed treatment: from 2 to 200 g per 100 kilogram of seed,        preferably from 3 to 150 g per 100 kilogram of seed;    -   for soil treatment: from 0.1 to 10,000 g/ha, preferably from 1        to 5,000 g/ha.

The doses herein indicated are given as illustrative Examples of methodaccording to the invention. A person skilled in the art will know how toadapt the application doses, notably according to the nature of theplant or crop to be treated.

Under specific conditions, for example according to the nature of thephytopathogenic fungus to be treated or controlled, a lower dose canoffer adequate protection. Certain climatic conditions, resistance orother factors like the nature of the phytopathogenic fungi or the degreeof infestation, for example, of the plants with these fungi, can requirehigher doses of combined active ingredients. The optimum dose usuallydepends on several factors, for example on the type of phytopathogenicfungus to be treated, on the type or level of development of theinfested plant, on the density of vegetation or alternatively on themethod of application.

Without it being limiting, the crop treated with the pesticidecomposition or combination according to the invention is, for example,grapevine, but this could be cereals, vegetables, lucerne, soybean,market garden crops, turf, wood, tree or horticultural plants.

The method of treatment according to the invention can also be useful totreat propagation material such as tubers or rhizomes, but also seeds,seedlings or seedlings pricking out and plants or plants pricking out.

This method of treatment can also be useful to treat roots. The methodof treatment according to the invention can also be useful to treat theover-ground parts of the plant such as trunks, stems or stalks, leaves,flowers and fruit of the concerned plant.

Among the plants that can be protected by the method according to theinvention, mention can be made of cotton; flax; vine; fruit or vegetablecrops such as Rosaceae sp. (for instance pip fruit such as apples andpears, but also stone fruit such as apricots, almonds and peaches),Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp.,Fagaceae sp., Moraceae sp., Oleaceae sp., Actimidaceae sp., Lauraceaesp., Musaceae sp. (for instance banana trees and plantins), Rubiaceaesp., Theaceae sp., Sterculiceae sp., Rutaceae sp. (for instance lemonsoranges and grapefruit); Solanaceae sp. (for instance tomatoes),Liliaceae sp., Asteraceae sp. (for instance lettuces), Umbelliferae sp.,Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp., Papilionaceae sp.(for instance peas), Rosaceae sp. (for instance strawberries); majorcrops such as Graminae sp. (for instance maize, lawn or cereals such aswheat, rice, barley and triticale), Asteraceae sp. (for instancesunflower), Cruciferae sp. (for instance colza), Fabacae sp. (forinstance peanuts), Papilionaceae sp. (for instance soybean), Solanaceaesp. (for instance potatoes), Chenopodiaceae sp. (for instancebeetroots); horticultural and forest crops; as well as geneticallymodified homologues of these crops.

The method of treatment according to the invention can be used in thetreatment of genetically modified organisms (GMOs), e.g. plants orseeds. Genetically modified plants (or transgenic plants) are plants inwhich a heterologous gene has been stably integrated into the genome.The expression “heterologous gene” essentially means a gene which isprovided or assembled outside the plant and when introduced in thenuclear, chloroplastic or mitochondrial genome gives the transformedplant new or improved agronomic or other properties by expressing aprotein or polypeptide of interest or by downregulating or silencingother gene(s) which are present in the plant (using for example,antisense technology, co suppression technology or RNAinterference—RNAi—technology). A heterologous gene that is located inthe genome is also called a transgene. A transgene that is defined byits particular location in the plant genome is called a transformationor transgenic event.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the active compounds and compositions which can be usedaccording to the invention, better plant growth, increased tolerance tohigh or low temperatures, increased tolerance to drought or to water orsoil salt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, bigger fruits, largerplant height, greener leaf color, earlier flowering, higher qualityand/or a higher nutritional value of the harvested products, highersugar concentration within the fruits, better storage stability and/orprocessability of the harvested products are possible, which exceed theeffects which were actually to be expected.

At certain application rates, the active compound combinations accordingto the invention may also have a strengthening effect in plants.Accordingly, they are also suitable for mobilizing the defense system ofthe plant against attack by unwanted phytopathogenic fungi and/ormicroorganisms and/or viruses. This may, if appropriate, be one of thereasons of the enhanced activity of the combinations according to theinvention, for example against fungi. Plant-strengthening(resistance-inducing) substances are to be understood as meaning, in thepresent context, those substances or combinations of substances whichare capable of stimulating the defense system of plants in such a waythat, when subsequently inoculated with unwanted phytopathogenic fungiand/or microorganisms and/or viruses, the treated plants display asubstantial degree of resistance to these unwanted phytopathogenic fungiand/or microorganisms and/or viruses. In the present case, unwantedphytopathogenic fungi and/or microorganisms and/or viruses are to beunderstood as meaning phytopathogenic fungi, bacteria and viruses. Thus,the substances according to the invention can be employed for protectingplants against attack by the abovementioned pathogens within a certainperiod of time after the treatment. The period of time within whichprotection is effected generally extends from 1 to 10 days, preferably 1to 7 days, after the treatment of the plants with the active compounds.

Plants and plant cultivars which are preferably to be treated accordingto the invention include all plants which have genetic material whichimpart particularly advantageous, useful traits to these plants (whetherobtained by breeding and/or biotechnological means).

Plants and plant cultivars which are also preferably to be treatedaccording to the invention are resistant against one or more bioticstresses, i.e. said plants show a better defense against animal andmicrobial pests, such as against nematodes, insects, mites,phytopathogenic fungi, bacteria, viruses and/or viroids.

Plants and plant cultivars which may also be treated according to theinvention are those plants which are resistant to one or more abioticstresses. Abiotic stress conditions may include, for example, drought,cold temperature exposure, heat exposure, osmotic stress, flooding,increased soil salinity, increased mineral exposure, ozon exposure, highlight exposure, limited availability of nitrogen nutrients, limitedavailability of phosphorus nutrients, shade avoidance.

Plants and plant cultivars which may also be treated according to theinvention, are those plants characterized by enhanced yieldcharacteristics. Increased yield in said plants can be the result of,for example, improved plant physiology, growth and development, such aswater use efficiency, water retention efficiency, improved nitrogen use,enhanced carbon assimilation, improved photosynthesis, increasedgermination efficiency and accelerated maturation. Yield can furthermorebe affected by improved plant architecture (under stress and non-stressconditions), including but not limited to, early flowering, floweringcontrol for hybrid seed production, seedling vigor, plant size,internode number and distance, root growth, seed size, fruit size, podsize, pod or ear number, seed number per pod or ear, seed mass, enhancedseed filling, reduced seed dispersal, reduced pod dehiscence and lodgingresistance. Further yield traits include seed composition, such ascarbohydrate content, protein content, oil content and composition,nutritional value, reduction in anti-nutritional compounds, improvedprocessability and better storage stability.

Plants that may be treated according to the invention are hybrid plantsthat already express the characteristic of heterosis or hybrid vigorwhich results in generally higher yield, vigor, health and resistancetowards biotic and abiotic stress factors. Such plants are typicallymade by crossing an inbred male-sterile parent line (the female parent)with another inbred male-fertile parent line (the male parent). Hybridseed is typically harvested from the male sterile plants and sold togrowers. Male sterile plants can sometimes (e.g. in corn) be produced bydetasseling, i.e. the mechanical removal of the male reproductive organs(or males flowers) but, more typically, male sterility is the result ofgenetic determinants in the plant genome. In that case, and especiallywhen seed is the desired product to be harvested from the hybrid plantsit is typically useful to ensure that male fertility in the hybridplants is fully restored. This can be accomplished by ensuring that themale parents have appropriate fertility restorer genes which are capableof restoring the male fertility in hybrid plants that contain thegenetic determinants responsible for male-sterility. Geneticdeterminants for male sterility may be located in the cytoplasm.Examples of cytoplasmic male sterility (CMS) were for instance describedin Brassica species (WO 1992/005251, WO 1995/009910, WO 1998/27806, WO2005/002324, WO 2006/021972 and U.S. Pat. No. 6,229,072). However,genetic determinants for male sterility can also be located in thenuclear genome. Male sterile plants can also be obtained by plantbiotechnology methods such as genetic engineering. A particularly usefulmeans of obtaining male-sterile plants is described in WO 1989/10396 inwhich, for example, a ribonuclease such as barnase is selectivelyexpressed in the tapetum cells in the stamens. Fertility can then berestored by expression in the tapetum cells of a ribonuclease inhibitorsuch as barstar (e.g. WO 1991/002069).

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may be treated according to the inventionare herbicide-tolerant plants, i.e. plants made tolerant to one or moregiven herbicides. Such plants can be obtained either by genetictransformation, or by selection of plants containing a mutationimparting such herbicide tolerance.

Herbicide-tolerant plants are for example glyphosate-tolerant plants,i.e. plants made tolerant to the herbicide glyphosate or salts thereof.Plants can be made tolerant to glyphosate through different means. Forexample, glyphosate-tolerant plants can be obtained by transforming theplant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphatesynthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutantCT7) of the bacterium Salmonella typhimurium (Comai et al., Science(1983), 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp.(Barry et al., Curr. Topics Plant Physiol. (1992), 7, 139-145), thegenes encoding a Petunia EPSPS (Shah et al., Science (1986), 233,478-481), a Tomato EPSPS (Gasser et al., J. Biol. Chem. (1988), 263,4280-4289), or an Eleusine EPSPS (WO 2001/66704). It can also be amutated EPSPS as described in for example EP-A 0837944, WO 2000/066746,WO 2000/066747 or WO 2002/026995. Glyphosate-tolerant plants can also beobtained by expressing a gene that encodes a glyphosate oxido-reductaseenzyme as described in U.S. Pat. No. 5,776,760 and U.S. Pat. No.5,463,175. Glyphosate-tolerant plants can also be obtained by expressinga gene that encodes a glyphosate acetyl transferase enzyme as describedin for example WO 2002/036782, WO 2003/092360, WO 2005/012515 and WO2007/024782. Glyphosate-tolerant plants can also be obtained byselecting plants containing naturally-occurring mutations of theabove-mentioned genes, as described in for example WO 2001/024615 or WO2003/013226.

Other herbicide resistant plants are for example plants that are madetolerant to herbicides inhibiting the enzyme glutamine synthase, such asbialaphos, phosphinothricin or glufosinate. Such plants can be obtainedby expressing an enzyme detoxifying the herbicide or a mutant glutaminesynthase enzyme that is resistant to inhibition. One such efficientdetoxifying enzyme is an enzyme encoding a phosphinothricinacetyltransferase (such as the bar or pat protein from Streptomycesspecies). Plants expressing an exogenous phosphinothricinacetyltransferase are for example described in U.S. Pat. No. 5,561,236;U.S. Pat. No. 5,648,477; U.S. Pat. No. 5,646,024; U.S. Pat. No.5,273,894; U.S. Pat. No. 5,637,489; U.S. Pat. No. 5,276,268; U.S. Pat.No. 5,739,082; U.S. Pat. No. 5,908,810 and U.S. Pat. No. 7,112,665.

Further herbicide-tolerant plants are also plants that are made tolerantto the herbicides inhibiting the enzyme hydroxyphenylpyruvatedioxygenase(HPPD). Hydroxyphenylpyruvatedioxygenases are enzymes that catalyze thereaction in which para-hydroxyphenylpyruvate (HPP) is transformed intohomogentisate. Plants tolerant to HPPD-inhibitors can be transformedwith a gene encoding a naturally-occurring resistant HPPD enzyme, or agene encoding a mutated HPPD enzyme as described in WO 1996/038567, WO1999/024585 and WO 1999/024586. Tolerance to HPPD-inhibitors can also beobtained by transforming plants with genes encoding certain enzymesenabling the formation of homogentisate despite the inhibition of thenative HPPD enzyme by the HPPD-inhibitor. Such plants and genes aredescribed in WO 1999/034008 and WO 2002/36787. Tolerance of plants toHPPD inhibitors can also be improved by transforming plants with a geneencoding an enzyme prephenate dehydrogenase in addition to a geneencoding an HPPD-tolerant enzyme, as described in WO 2004/024928.

Still further herbicide resistant plants are plants that are madetolerant to acetolactate synthase (ALS) inhibitors. Known ALS-inhibitorsinclude, for example, sulfonylurea, imidazolinone, triazolopyrimidines,pyrimidinyloxy(thio)benzoates, and/or sulfonylaminocarbonyltriazolinoneherbicides. Different mutations in the ALS enzyme (also known asacetohydroxyacid synthase, AHAS) are known to confer tolerance todifferent herbicides and groups of herbicides, as described for examplein Tranel and Wright, Weed Science (2002), 50, 700-712, but also, inU.S. Pat. No. 5,605,011, U.S. Pat. No. 5,378,824, U.S. Pat. No.5,141,870, and U.S. Pat. No. 5,013,659. The production ofsulfonylurea-tolerant plants and imidazolinone-tolerant plants isdescribed in U.S. Pat. No. 5,605,011; U.S. Pat. No. 5,013,659; U.S. Pat.No. 5,141,870; U.S. Pat. No. 5,767,361; U.S. Pat. No. 5,731,180; U.S.Pat. No. 5,304,732; U.S. Pat. No. 4,761,373; U.S. Pat. No. 5,331,107;U.S. Pat. No. 5,928,937; and U.S. Pat. No. 5,378,824; and internationalpublication WO 1996/033270. Other imidazolinone-tolerant plants are alsodescribed in for example WO 2004/040012, WO 2004/106529, WO 2005/020673,WO 2005/093093, WO 2006/007373, WO 2006/015376, WO 2006/024351, and WO2006/060634. Further sulfonylurea- and imidazolinone-tolerant plants arealso described in for example WO 2007/024782.

Other plants tolerant to imidazolinone and/or sulfonylurea can beobtained by induced mutagenesis, selection in cell cultures in thepresence of the herbicide or mutation breeding as described for examplefor soybeans in U.S. Pat. No. 5,084,082, for rice in WO 1997/41218, forsugar beet in U.S. Pat. No. 5,773,702 and WO 1999/057965, for lettuce inU.S. Pat. No. 5,198,599, or for sunflower in WO 2001/065922.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are insect-resistant transgenic plants, i.e. plants maderesistant to attack by certain target insects. Such plants can beobtained by genetic transformation, or by selection of plants containinga mutation imparting such insect resistance.

An “insect-resistant transgenic plant”, as used herein, includes anyplant containing at least one transgene comprising a coding sequenceencoding:

-   -   1) an insecticidal crystal protein from Bacillus thuringiensis        or an insecticidal portion thereof, such as the insecticidal        crystal proteins listed by Crickmore et al., Microbiology and        Molecular Biology Reviews (1998), 62, 807-813, updated by        Crickmore et al. (2005) at the Bacillus thuringiensis toxin        nomenclature, online at:        http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), or        insecticidal portions thereof, e.g., proteins of the Cry protein        classes Cry1Ab, Cry1Ac, Cry1F, Cry2Ab, Cry3Aa, or Cry3Bb or        insecticidal portions thereof; or    -   2) a crystal protein from Bacillus thuringiensis or a portion        thereof which is insecticidal in the presence of a second other        crystal protein from Bacillus thuringiensis or a portion        thereof, such as the binary toxin made up of the Cry34 and Cry35        crystal proteins (Moellenbeck et al., Nat. Biotechnol. (2001),        19, 668-72; Schnepf et al., Applied Environm. Microbiol. (2006),        71, 1765-1774); or    -   3) a hybrid insecticidal protein comprising parts of different        insecticidal crystal proteins from Bacillus thuringiensis, such        as a hybrid of the proteins of 1) above or a hybrid of the        proteins of 2) above, e.g., the Cry1A.105 protein produced by        corn event MON98034 (WO 2007/027777); or    -   4) a protein of any one of 1) to 3) above wherein some,        particularly 1 to 10, amino acids have been replaced by another        amino acid to obtain a higher insecticidal activity to a target        insect species, and/or to expand the range of target insect        species affected, and/or because of changes introduced into the        encoding DNA during cloning or transformation, such as the        Cry3Bb1 protein in corn events MON863 or MON88017, or the Cry3A        protein in corn event MIR604;    -   5) an insecticidal secreted protein from Bacillus thuringiensis        or Bacillus cereus, or an insecticidal portion thereof, such as        the vegetative insecticidal (VIP) proteins listed at:        http://www.lifesci.sussex.ac.uk/home/Neil_Crickmore/Bt/vip.html,        e.g., proteins from the VIP3Aa protein class; or    -   6) a secreted protein from Bacillus thuringiensis or Bacillus        cereus which is insecticidal in the presence of a second        secreted protein from Bacillus thuringiensis or B. cereus, such        as the binary toxin made up of the VIP1A and VIP2A proteins (WO        1994/21795); or    -   7) a hybrid insecticidal protein comprising parts from different        secreted proteins from Bacillus thuringiensis or Bacillus        cereus, such as a hybrid of the proteins in 1) above or a hybrid        of the proteins in 2) above; or    -   8) a protein of any one of 1) to 3) above wherein some,        particularly 1 to 10, amino acids have been replaced by another        amino acid to obtain a higher insecticidal activity to a target        insect species, and/or to expand the range of target insect        species affected, and/or because of changes introduced into the        encoding DNA during cloning or transformation (while still        encoding an insecticidal protein), such as the VIP3Aa protein in        cotton event COT102.

Of course, an insect-resistant transgenic plant, as used herein, alsoincludes any plant comprising a combination of genes encoding theproteins of any one of the above classes 1 to 8. In one embodiment, aninsect-resistant plant contains more than one transgene encoding aprotein of any one of the above classes 1 to 8, to expand the range oftarget insect species affected when using different proteins directed atdifferent target insect species, or to delay insect resistancedevelopment to the plants by using different proteins insecticidal tothe same target insect species but having a different mode of action,such as binding to different receptor binding sites in the insect.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are tolerant to abiotic stresses. Such plants can be obtainedby genetic transformation, or by selection of plants containing amutation imparting such stress resistance. Particularly useful stresstolerance plants include:

-   -   a. plants which contain a transgene capable of reducing the        expression and/or the activity of poly(ADP-ribose)polymerase        (PARP) gene in the plant cells or plants as described in WO        2000/004173 or WO2006/045633 or PCT/EP07/004,142.    -   b. plants which contain a stress tolerance enhancing transgene        capable of reducing the expression and/or the activity of the        PARG encoding genes of the plants or plants cells, as described        e.g. in WO 2004/090140.    -   c. plants which contain a stress tolerance enhancing transgene        coding for a plant-functional enzyme of the nicotinamide adenine        dinucleotide salvage synthesis pathway including nicotinamidase,        nicotinate phosphoribosyltransferase, nicotinic acid        mononucleotide adenyl transferase, nicotinamide adenine        dinucleotide synthetase or nicotine amide        phosphoribosyltransferase as described e.g. in WO2006/032469 or        WO 2006/133827 or PCT/EP07/002,433.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention show altered quantity, quality and/or storage-stability of theharvested product and/or altered properties of specific ingredients ofthe harvested product such as:

-   -   1) transgenic plants which synthesize a modified starch, which        in its physical-chemical characteristics, in particular the        amylose content or the amylose/amylopectin ratio, the degree of        branching, the average chain length, the side chain        distribution, the viscosity behaviour, the gelling strength, the        starch grain size and/or the starch grain morphology, is changed        in comparison with the synthesised starch in wild type plant        cells or plants, so that this is better suited for special        applications. Said transgenic plants synthesizing a modified        starch are disclosed, for example, in EP 0571427, WO        1995/004826, EP 0719338, WO 1996/15248, WO 1996/19581, WO        1996/27674, WO 1997/11188, WO 1997/26362, WO 1997/32985, WO        1997/42328, WO 1997/44472, WO 1997/45545, WO 1998/27212, WO        1998/40503, WO99/58688, WO 1999/58690, WO 1999/58654, WO        2000/008184, WO 2000/008185, WO 2000/008175, WO 2000/28052, WO        2000/77229, WO 2001/12782, WO 2001/12826, WO 2002/101059, WO        2003/071860, WO 2004/056999, WO 2005/030942, WO 2005/030941, WO        2005/095632, WO 2005/095617, WO 2005/095619, WO 2005/095618, WO        2005/123927, WO 2006/018319, WO 2006/103107, WO 2006/108702, WO        2007/009823, WO 2000/22140, WO 2006/063862, WO 2006/072603, WO        2002/034923, EP 06090134.5, EP 06090228.5, EP 06090227.7, EP        07090007.1, EP 07090009.7, WO 2001/14569, WO 2002/79410, WO        2003/33540, WO 2004/078983, WO 2001/19975, WO 1995/26407, WO        1996/34968, WO 1998/20145, WO 1999/12950, WO 1999/66050, WO        1999/53072, U.S. Pat. No. 6,734,341, WO 2000/11192, WO        1998/22604, WO 1998/32326, WO 2001/98509, WO 2001/98509, WO        2005/002359, U.S. Pat. No. 5,824,790, U.S. Pat. No. 6,013,861,        WO 1994/004693, WO 1994/009144, WO 1994/11520, WO 1995/35026, WO        1997/20936.    -   2) transgenic plants which synthesize non starch carbohydrate        polymers or which synthesize non starch carbohydrate polymers        with altered properties in comparison to wild type plants        without genetic modification. Examples are plants producing        polyfructose, especially of the inulin and levan-type, as        disclosed in EP 0663956, WO 1996/001904, WO 1996/021023, WO        1998/039460, and WO 1999/024593, plants producing alpha 1,4        glucans as disclosed in WO 1995/031553, US 2002/031826, U.S.        Pat. No. 6,284,479, U.S. Pat. No. 5,712,107, WO 1997/047806, WO        1997/047807, WO 1997/047808 and WO 2000/014249, plants producing        alpha-1,6 branched alpha-1,4-glucans, as disclosed in WO        2000/73422, plants producing alternan, as disclosed in WO        2000/047727, EP 06077301.7, U.S. Pat. No. 5,908,975 and EP        0728213,    -   3) transgenic plants which produce hyaluronan, as for example        disclosed in WO 2006/032538, WO 2007/039314, WO 2007/039315, WO        2007/039316, JP 2006/304779, and WO 2005/012529.

Plants or plant cultivars (that can be obtained by plant biotechnologymethods such as genetic engineering) which may also be treated accordingto the invention are plants, such as cotton plants, with altered fibercharacteristics. Such plants can be obtained by genetic transformation,or by selection of plants contain a mutation imparting such alteredfiber characteristics and include:

-   -   a) Plants, such as cotton plants, containing an altered form of        cellulose synthase genes as described in WO 1998/000549    -   b) Plants, such as cotton plants, containing an altered form of        rsw2 or rsw3 homologous nucleic acids as described in        WO2004/053219    -   c) Plants, such as cotton plants, with increased expression of        sucrose phosphate synthase as described in WO 2001/017333    -   d) Plants, such as cotton plants, with increased expression of        sucrose synthase as described in WO02/45485    -   e) Plants, such as cotton plants, wherein the timing of the        plasmodesmatal gating at the basis of the fiber cell is altered,        e.g. through downregulation of fiberselective β 1,3-glucanase as        described in WO2005/017157    -   f) Plants, such as cotton plants, having fibers with altered        reactivity, e.g. through the expression of        N-acteylglucosaminetransferase gene including nodC and        chitinsynthase genes as described in WO2006/136351

Plants or plant cultivars (that can be obtained by plant biotechnologymethods such as genetic engineering) which may also be treated accordingto the invention are plants, such as oilseed rape or related Brassicaplants, with altered oil profile characteristics. Such plants can beobtained by genetic transformation or by selection of plants contain amutation imparting such altered oil characteristics and include:

-   -   a) Plants, such as oilseed rape plants, producing oil having a        high oleic acid content as described e.g. in U.S. Pat. No.        5,969,169, U.S. Pat. No. 5,840,946 or U.S. Pat. No. 6,323,392 or        U.S. Pat. No. 6,063,947    -   b) Plants such as oilseed rape plants, producing oil having a        low linolenic acid content as described in U.S. Pat. No.        6,270,828, U.S. Pat. No. 6,169,190 or U.S. Pat. No. 5,965,755    -   c) Plant such as oilseed rape plants, producing oil having a low        level of saturated fatty acids as described e.g. in U.S. Pat.        No. 5,434,283

Particularly useful transgenic plants which may be treated according tothe invention are plants which comprise one or more genes which encodeone or more toxins, such as the following which are sold under the tradenames YIELD GARD® (for example maize, cotton, soya beans), KnockOut®(for example maize), BiteGard® (for example maize), Bt-Xtra® (forexample maize), StarLink® (for example maize), Bollgard® (cotton),Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (for example maize),Protecta® and NewLeaf® (potato). Examples of herbicide-tolerant plantswhich may be mentioned are maize varieties, cotton varieties and soyabean varieties which are sold under the trade names Roundup Ready®(tolerance to glyphosate, for example maize, cotton, soya bean), LibertyLink® (tolerance to phosphinotricin, for example oilseed rape), IMI®(tolerance to imidazolinones) and STS® (tolerance to sulphonylureas, forexample maize). Herbicide-resistant plants (plants bred in aconventional manner for herbicide tolerance) which may be mentionedinclude the varieties sold under the name Clearfield® (for examplemaize).

Particularly useful transgenic plants which may be treated according tothe invention are plants containing transformation events, orcombination of transformation events, that are listed for example in thedatabases from various national or regional regulatory agencies (see forexample http://gmoinfo.jrc.it/gmp_browse.aspx andhttp://www.agbios.com/dbase.php).

The composition according to the invention can also be used againstfungal diseases liable to grow on or inside timber. The term “timber”means all types of species of wood and all types of working of this woodintended for construction, for example solid wood, high-density wood,laminated wood and plywood. The method for treating timber according tothe invention mainly consists in contacting one or more compoundsaccording to the invention or a composition according to the invention;this includes for example direct application, spraying, dipping,injection or any other suitable means.

Among the diseases of plants or crops that can be controlled by themethod according to the invention, mention can be made of:

Powdery mildew diseases such as:

-   -   Blumeria diseases, caused for example by Blumeria graminis;    -   Podosphaera diseases, caused for example by Podosphaera        leucotricha;    -   Sphaerotheca diseases, caused for example by Sphaerotheca        fuliginea;    -   Uncinula diseases, caused for example by Uncinula necator;        Rust diseases such as:    -   Gymnosporangium diseases, caused for example by Gymnosporangium        sabinae;    -   Hemileia diseases, caused for example by Hemileia vastatrix;    -   Phakopsora diseases, caused for example by Phakopsora pachyrhizi        or Phakopsora meibomiae;    -   Puccinia diseases, caused for example by Puccinia recondita;    -   Uromyces diseases, caused for example by Uromyces        appendiculatus;        Oomycete diseases such as:    -   Bremia diseases, caused for example by Bremia lactucae;    -   Peronospora diseases, caused for example by Peronospora pisi        or P. brassicae;    -   Phytophthora diseases, caused for example by Phytophthora        infestans;    -   Plasmopara diseases, caused for example by Plasmopara viticola;    -   Pseudoperonospora diseases, caused for example by        Pseudoperonospora humuli or Pseudoperonospora cubensis;    -   Pythium diseases, caused for example by Pythium ultimum;        Leafspot, leaf blotch and leaf blight diseases such as:    -   Alternaria diseases, caused for example by Alternaria solani;    -   Cercospora diseases, caused for example by Cercospora beticola;    -   Cladiosporum diseases, caused for example by Cladiosporium        cucumerinum;    -   Cochliobolus diseases, caused for example by Cochliobolus        sativus;    -   Colletotrichum diseases, caused for example by Colletotrichum        lindemuthanium;    -   Cycloconium diseases, caused for example by Cycloconium        oleaginum;    -   Diaporthe diseases, caused for example by Diaporthe citri;    -   Elsinoe diseases, caused for example by Elsinoe fawcettii;    -   Gloeosporium diseases, caused for example by Gloeosporium        laeticolor;    -   Glomerella diseases, caused for example by Glomerella cingulata;    -   Guignardia diseases, caused for example by Guignardia bidwelli;    -   Leptosphaeria diseases, caused for example by Leptosphaeria        maculans; Leptosphaeria nodorum;    -   Magnaporthe diseases, caused for example by Magnaporthe grisea;    -   Mycosphaerella diseases, caused for example by Mycosphaerella        graminicola; Mycosphaerella arachidicola; Mycosphaerella        fijiensis;    -   Phaeosphaeria diseases, caused for example by Phaeosphaeria        nodorum;    -   Pyrenophora diseases, caused for example by Pyrenophora teres;    -   Ramularia diseases, caused for example by Ramularia collo-cygni;    -   Rhynchosporium diseases, caused for example by Rhynchosporium        secalis;    -   Septoria diseases, caused for example by Septoria apii or        Septoria lycopercisi;    -   Typhula diseases, caused for example by Typhula incarnata;    -   Venturia diseases, caused for example by Venturia inaequalis;        Root and stem diseases such as:    -   Corticium diseases, caused for example by Corticium graminearum;    -   Fusarium diseases, caused for example by Fusarium oxysporum;    -   Gaeumannomyces diseases, caused for example by Gaeumannomyces        graminis;    -   Rhizoctonia diseases, caused for example by Rhizoctonia solani;    -   Tapesia diseases, caused for example by Tapesia acuformis;    -   Thielaviopsis diseases, caused for example by Thielaviopsis        basicola;        Ear and panicle diseases such as:    -   Alternaria diseases, caused for example by Alternaria spp.;    -   Aspergillus diseases, caused for example by Aspergillus flavus;    -   Cladosporium diseases, caused for example by Cladosporium spp.;    -   Claviceps diseases, caused for example by Claviceps purpurea;    -   Fusarium diseases, caused for example by Fusarium culmorum;    -   Gibberella diseases, caused for example by Gibberella zeae;    -   Monographella diseases, caused for example by Monographella        nivalis;        Smut and bunt diseases such as:    -   Sphacelotheca diseases, caused for example by Sphacelotheca        reiliana;    -   Tilletia diseases, caused for example by Tilletia caries;    -   Urocystis diseases, caused for example by Urocystis occulta;    -   Ustilago diseases, caused for example by Ustilago nuda;        Fruit rot and mould diseases such as:    -   Aspergillus diseases, caused for example by Aspergillus flavus;    -   Botrytis diseases, caused for example by Botrytis cinerea;    -   Penicillium diseases, caused for example by Penicillium        expansum;    -   Sclerotinia diseases, caused for example by Sclerotinia        sclerotiorum;    -   Verticilium diseases, caused for example by Verticilium        alboatrum;        Seed and soilborne decay, mould, wilt, rot and damping-off        diseases:    -   Alternaria diseases, caused for example by Alternaria        brassicicola;    -   Aphanomyces diseases, caused for example by Aphanomyces        euteiches    -   Ascochyta diseases, caused for example by Ascochyta lentis    -   Aspergillus diseases, caused for example by Aspergillus flavus    -   Cladosporium diseases, caused for example by Cladosporium        herbarum    -   Cochliobolus diseases, caused for example by Cochliobolus        sativus (Conidiaform: Drechslera, Bipolaris Syn:        Helminthosporium);    -   Colletotrichum diseases, caused for example by Colletotrichum        coccodes;    -   Fusarium diseases, caused for example by Fusarium culmorum;    -   Gibberella diseases, caused for example by Gibberella zeae;    -   Macrophomina diseases, caused for example by Macrophomina        phaseolina    -   Monographella diseases, caused for example by Monographella        nivalis;    -   Penicillium diseases, caused for example by Penicillium expansum    -   Phoma diseases, caused for example by Phoma lingam    -   Phomopsis diseases, caused for example by Phomopsis sojae;    -   Phytophthora diseases, caused for example by Phytophthora        cactorum;    -   Pyrenophora diseases, caused for example by Pyrenophora graminea    -   Pyricularia diseases, caused for example by Pyricularia oryzae;    -   Pythium diseases, caused for example by Pythium ultimum;    -   Rhizoctonia diseases, caused for example by Rhizoctonia solani;    -   Rhizopus diseases, caused for example by Rhizopus oryzae    -   Sclerotium diseases, caused for example by Sclerotium rolfsii;    -   Septoria diseases, caused for example by Septoria nodorum;    -   Typhula diseases, caused for example by Typhula incarnata;    -   Verticillium diseases, caused for example by Verticillium        dahliae;        Canker, broom and dieback diseases such as:    -   Nectria diseases, caused for example by Nectria galligena;        Blight diseases such as:    -   Monilinia diseases, caused for example by Monilinia laxa;        Leaf blister or leaf curl diseases such as:    -   Taphrina diseases, caused for example by Taphrina deformans;        Decline diseases of wooden plants such as:    -   Esca diseases, caused for example by Phaemoniella clamydospora;    -   Eutypa dyeback, caused for example by Eutypa lata;    -   Dutch elm disease, caused for example by Ceratocystsc ulmi;        Diseases of flowers and Seeds such as:    -   Botrytis diseases, caused for example by Botrytis cinerea;        Diseases of tubers such as:    -   Rhizoctonia diseases, caused for example by Rhizoctonia solani    -   Helminthosporium diseases, caused for example by        Helminthosporium solani.

The compounds according to the invention can also be used for thepreparation of composition useful to curatively or preventively treathuman or animal fungal diseases such as, for example, mycoses,dermatoses, trichophyton diseases and candidiases or diseases caused byAspergillus spp., for example Aspergillus fumigatus.

The various aspects of the invention will now be illustrated withreference to the following table 1 of compound examples and thefollowing preparation or efficacy examples.

The following table 1 illustrates in a non limiting manner examples ofcompounds according to the invention.

In table 1 we use the following abbreviations for specified claimedelements “Het” of the generic structure (I) of the invention:

TABLE 1 Ex. A

Het Q MW_measured log p 1 1-methyl-1H-tetrazol-5-yl phenyl Het¹4-ethoxyphenyl  458* 3.69 2 1-methyl-1H-tetrazol-5-yl phenyl Het¹[5-methyl-3-(trifluoromethyl)-1H-  500* 3.48 pyrazol-1-yl]methyl 31-methyl-1H-tetrazol-5-yl phenyl Het¹ difluoro(phenoxy)methyl 3.94 41-methyl-1H-tetrazol-5-yl phenyl Het¹ difluoro(3-methylphenoxy)methyl4.26 5 1-methyl-1H-tetrazol-5-yl phenyl Het¹difluoro(4-methylphenoxy)methyl 4.26 6 1-methyl-1H-tetrazol-5-yl phenylHet¹ difluoro(phenylsulfanyl)methyl 4.11 7 1-methyl-1H-tetrazol-5-ylphenyl Het¹ difluoro[(4- 4.44 methylphenyl)sulfanyl]methyl 81-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹ 2-cyclopentylethyl 4524.26 9 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹ 2-cyclohexylethyl466 4.65 10 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹ 2-phenoxyethyl476 3.64 11 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹prop-2-en-1-yloxy 412 3.29 12 1-methyl-1H-tetrazol-5-yl 3-fluorophenylHet¹ but-3-en-1-yloxy 426 3.58 13 1-methyl-1H-tetrazol-5-yl3-fluorophenyl Het¹ but-3-yn-1-yloxy 424 3.21 141-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹ but-2-yn-1-yloxy 424 3.3715 1-methyl-1H-tetrazol-5-yl phenyl Het² but-3-yn-1-yloxy 412 2.88 161-methyl-1H-tetrazol-5-yl phenyl Het² prop-2-yn-1-yloxy 398 2.75 175-methyl-1H-tetrazol-1-yl phenyl Het¹ but-3-yn-1-yloxy 406 3.15 185-methyl-1H-tetrazol-1-yl phenyl Het¹ but-2-yn-1-yloxy 406 3.29 195-methyl-1H-tetrazol-1-yl phenyl Het¹ but-3-en-1-yloxy 408 3.55 205-methyl-1H-tetrazol-1-yl phenyl Het¹ 4-chlorobutoxy 444 3.73 215-methyl-1H-tetrazol-1-yl phenyl Het¹ cycloheptyloxy 450 4.71 225-methyl-1H-tetrazol-1-yl phenyl Het¹ 2-(benzyloxy)ethoxy 488 3.83 235-methyl-1H-tetrazol-1-yl 3-fluorophenyl Het¹ but-3-yn-1-yloxy 424 3.2124 5-methyl-1H-tetrazol-1-yl 3-fluorophenyl Het¹ but-2-yn-1-yloxy 4243.39 25 5-methyl-1H-tetrazol-1-yl 3-fluorophenyl Het¹2-(benzyloxy)ethoxy 506 3.92 26 5-methyl-1H-tetrazol-1-yl 3-fluorophenylHet² 2-(benzyloxy)ethoxy 512 3.67 27 5-methyl-1H-tetrazol-1-yl3-fluorophenyl Het¹ but-3-en-1-yloxy 426 3.67 285-methyl-1H-tetrazol-1-yl 3-fluorophenyl Het¹ prop-2-en-1-yloxy 412 3.3729 5-methyl-1H-tetrazol-1-yl 3-fluorophenyl Het² prop-2-en-1-yloxy 4183.13 30 5-methyl-1H-tetrazol-1-yl 3-fluorophenyl Het¹ 4-chlorobutoxy 4623.83 31 5-methyl-1H-tetrazol-1-yl 3-fluorophenyl Het² 4-chlorobutoxy 4683.55 32 5-methyl-1H-tetrazol-1-yl 3-fluorophenyl Het¹ cycloheptyloxy 4684.78 33 5-methyl-1H-tetrazol-1-yl 3-fluorophenyl Het² cycloheptyloxy 4744.39 34 5-methyl-1H-tetrazol-1-yl phenyl Het¹ pent-4-yn-1-yl 404 3.04 355-methyl-1H-tetrazol-1-yl 3-fluorophenyl Het¹ pent-4-yn-1-yl 422 3.15 365-methyl-1H-tetrazol-1-yl 3-fluorophenyl Het² pent-4-yn-1-yl 428 3.04 375-methyl-1H-tetrazol-1-yl phenyl Het¹ thiophen-2-ylmethyl 434 3.29 385-methyl-1H-tetrazol-1-yl 3-fluorophenyl Het¹ thiophen-2-ylmethyl 4523.39 39 5-methyl-1H-tetrazol-1-yl 3-fluorophenyl Het²thiophen-2-ylmethyl 458 3.23 40 5-methyl-1H-tetrazol-1-yl phenyl Het¹cyclohexylmethyl 434 4.12 41 5-methyl-1H-tetrazol-1-yl 3-fluorophenylHet¹ cyclohexylmethyl 452 4.23 42 5-methyl-1H-tetrazol-1-yl phenyl Het¹2-cyclohexylethyl 448 4.62 43 5-methyl-1H-tetrazol-1-yl 3-fluorophenylHet¹ 2-cyclohexylethyl 466 4.7 44 5-methyl-1H-tetrazol-1-yl phenyl Het¹2-cyclopentylethyl 434 4.25 45 5-methyl-1H-tetrazol-1-yl 3-fluorophenylHet¹ 2-cyclopentylethyl 452 4.33 46 5-methyl-1H-tetrazol-1-yl phenylHet¹ phenoxymethyl 444 3.58 47 5-methyl-1H-tetrazol-1-yl 3-fluorophenylHet¹ phenoxymethyl 462 3.67 48 5-methyl-1H-tetrazol-1-yl phenyl Het¹difluoro(phenylsulfanyl)methyl 496 4.2 49 1-methyl-1H-tetrazol-5-ylphenyl Het¹ 2-(5-chlorothiophen-2-yl)ethyl 482 3.99 501-methyl-1H-tetrazol-5-yl phenyl Het¹ tetrahydro-2H-pyran-2-yl 422 3.4651 1-methyl-1H-tetrazol-5-yl phenyl Het¹ 2-cyclopentylethyl 434 4.11 521-methyl-1H-tetrazol-5-yl phenyl Het¹ 2-cyclohexylethyl 448 4.51 531-methyl-1H-tetrazol-5-yl phenyl Het¹ 2-phenoxyethyl 458 3.78 541-methyl-1H-tetrazol-5-yl phenyl Het¹ 3-(2,2-dichloroethenyl)-2,2- 5014.62 dimethylcyclopropyl 55 1-methyl-1H-tetrazol-5-yl phenyl Het¹pent-4-yn-1-yl 404 2.98 56 1-methyl-1H-tetrazol-5-yl phenyl Het¹prop-2-en-1-yloxy 394 3.21 57 1-methyl-1H-tetrazol-5-yl phenyl Het¹but-3-en-1-yloxy 408 3.51 58 1-methyl-1H-tetrazol-5-yl phenyl Het¹but-2-yn-1-yloxy 406 3.25 59 1-methyl-1H-tetrazol-5-yl phenyl Het¹prop-2-yn-1-yloxy 392 2.9 60 1-methyl-1H-tetrazol-5-yl phenyl Het¹4-propylphenyl 456 4.39 61 1-methyl-1H-tetrazol-5-yl phenyl Het¹2-phenylcyclopropyl 454 3.85 62 1-methyl-1H-tetrazol-5-yl phenyl Het¹bicyclo[2,2,1]hept-2-ylmethyl 446 4.16 63 1-methyl-1H-tetrazol-5-ylphenyl Het¹ 3-cyclohexylpropyl 462 4.94 64 1-methyl-1H-tetrazol-5-ylphenyl Het¹ phenoxymethyl 444 3.53 65 1-methyl-1H-tetrazol-5-yl phenylHet¹ cyclohexylmethyl 434 4.04 66 1-methyl-1H-tetrazol-5-yl phenyl Het¹2-(benzyloxy)ethoxy 488 3.76 67 1-methyl-1H-tetrazol-5-yl phenyl Het¹4-chlorobutoxy 444 3.67 68 1-methyl-1H-tetrazol-5-yl phenyl Het¹2-fluoroethoxy 400 2.78 69 5-methyl-1H-tetrazol-1-yl phenyl Het²4-propylphenyl 4.36 70 5-methyl-1H-tetrazol-1-yl phenyl Het²1-phenylcyclopropyl 460 3.94 71 5-methyl-1H-tetrazol-1-yl phenyl Het²2-phenylcyclopropyl 3.78 72 5-methyl-1H-tetrazol-1-yl phenyl Het²2-(5-chlorothiophen-2-yl)ethyl 488 3.83 73 5-methyl-1H-tetrazol-1-ylphenyl Het² tetrahydro-2H-pyran-4-yl 2.49 74 5-methyl-1H-tetrazol-1-ylphenyl Het² 3-chlorophenyl 454 3.76 75 5-methyl-1H-tetrazol-1-yl phenylHet² 1-phenoxyethyl 464 3.53 76 5-methyl-1H-tetrazol-1-yl phenyl Het²3-fluorophenyl 438 3.42 77 5-methyl-1H-tetrazol-1-yl phenyl Het²-4-[(2R,3aR,5S,6aS)-hexahydro- 4.21 2,5-methanopentalen-3a(1H)-yl 785-methyl-1H-tetrazol-1-yl phenyl Het² bicyclo[2,2,1]hept-5-en-2-yl 3.3979 5-methyl-1H-tetrazol-1-yl phenyl Het² pentadecafluoroheptyl 5.17 805-methyl-1H-tetrazol-1-yl phenyl Het² 4-ethylphenyl 3.96 815-methyl-1H-tetrazol-1-yl phenyl Het² 6-chloropyridin-3-yl 3.13 825-methyl-1H-tetrazol-1-yl phenyl Het² thiophen-2-yl 426 3.19 835-methyl-1H-tetrazol-1-yl phenyl Het² cyclohex-3-en-1-yl 3.42 845-methyl-1H-tetrazol-1-yl phenyl Het² cyclopropylmethyl 2.9 855-methyl-1H-tetrazol-1-yl phenyl Het² undecafluorocyclohexyl 624 4.44 865-methyl-1H-tetrazol-1-yl phenyl Het² {[(1R,2S,5R)-5-methyl-2- 5.48(propan-2- yl)cyclohexyl]oxy}methyl 87 5-methyl-1H-tetrazol-1-yl phenylHet² 3-(2,2-dichloroethenyl)-2,2- 4.49 dimethylcyclopropyl 885-methyl-1H-tetrazol-1-yl phenyl Het² 2-methylbicyclo[2,2,1]hept-2-yl4.19 89 5-methyl-1H-tetrazol-1-yl phenyl Het² difluoro[(4- 4.21methylphenyl)sulfanyl]methyl 90 5-methyl-1H-tetrazol-1-yl phenyl Het²difluoro(3-methylphenoxy)methyl 500 4.04 91 5-methyl-1H-tetrazol-1-ylphenyl Het² difluoro(4-methylphenoxy)methyl 4.09 925-methyl-1H-tetrazol-1-yl phenyl Het² 4-ethoxyphenyl 3.71 935-methyl-1H-tetrazol-1-yl phenyl Het²tricyclo[3.3.1.1^(3,7)]dec-1-ylmethyl 4.77 94 5-methyl-1H-tetrazol-1-ylphenyl Het² (1S,3R,5R,7S)- 492 4.73tricyclo[3.3.1.1^(3,7)]dec-1-ylmethyl 95 5-methyl-1H-tetrazol-1-ylphenyl Het² methoxy(phenyl)methyl 96 5-methyl-1H-tetrazol-1-yl phenylHet² bicyclo[2.2.1]hept-2-ylmethyl 452 4.01 97 5-methyl-1H-tetrazol-1-ylphenyl Het² [5-methyl-3-(trifluoromethyl)-1H- 3.37 pyrazol-1-yl]methyl98 5-methyl-1H-tetrazol-1-yl phenyl Het² (2-chlorophenoxy)methyl 4843.62 99 5-methyl-1H-tetrazol-1-yl phenyl Het² 4-butoxyphenyl 4.51 1005-methyl-1H-tetrazol-1-yl phenyl Het² (1,1,1-trichloro-2-methylpropan-518 4.39 2-yl)oxy 101 5-methyl-1H-tetrazol-1-yl phenyl Het²4-(acetyloxy)butoxy 3.04 102 5-methyl-1H-tetrazol-1-yl phenyl Het²(1,7,7-trimethylbicyclo[2.2.1] 496 4.97 hept-2-yl)oxy 1035-methyl-1H-tetrazol-1-yl phenyl Het² (2-methylprop-2-en-1-yl)oxy 3.33104 5-methyl-1H-tetrazol-1-yl phenyl Het² prop-1-en-2-yloxy 400 2.96 1055-methyl-1H-tetrazol-1-yl phenyl Het² 2,2,2-trichloroethoxy 490 3.71 1065-methyl-1H-tetrazol-1-yl phenyl Het¹ morpholin-4-yl 423 2.17 1075-methyl-1H-tetrazol-1-yl phenyl Het¹ prop-1-en-2-yloxy 394 3.21 1085-methyl-1H-tetrazol-1-yl phenyl Het¹ 2,2,2-trichloroethoxy 484 4.06 1095-methyl-1H-tetrazol-1-yl phenyl Het¹ piperidin-1-yl 421 2.69 1105-methyl-1H-tetrazol-1-yl phenyl Het¹ 1-phenylcyclopropyl 454 2.55 1115-methyl-1H-tetrazol-1-yl phenyl Het¹ 2-phenylethenyl 440 3.78 1125-methyl-1H-tetrazol-1-yl phenyl Het¹ 2-phenylcyclopropyl 454 3.94 1135-methyl-1H-tetrazol-1-yl phenyl Het¹ 2-(5-chlorothiophen-2-yl)ethyl 4824.06 114 5-methyl-1H-tetrazol-1-yl phenyl Het¹ 3-chlorophenyl 448 3.92115 5-methyl-1H-tetrazol-1-yl phenyl Het¹ 1-phenoxyethyl 458 3.85 1165-methyl-1H-tetrazol-1-yl phenyl Het¹ 3-fluorophenyl 432 3.48 1175-methyl-1H-tetrazol-1-yl phenyl Het¹ -4-[(2R,3aR,5S,6aS)-hexahydro- 4584.29 2,5-methanopentalen-3a(1H)-yl 118 5-methyl-1H-tetrazol-1-yl phenylHet¹ bicyclo[2.2.1]hept-5-en-2-yl 430 3.55 119 5-methyl-1H-tetrazol-1-ylphenyl Het¹ pentadecafluoroheptyl 706 5.93 120 5-methyl-1H-tetrazol-1-ylphenyl Het¹ 4-ethylphenyl 442 4.01 121 5-methyl-1H-tetrazol-1-yl phenylHet¹ 6-chloropyridin-3-yl 449 3.15 122 5-methyl-1H-tetrazol-1-yl phenylHet¹ thiophen-2-yl 420 3.29 123 5-methyl-1H-tetrazol-1-yl phenyl Het¹cyclohex-3-en-1-yl 418 3.58 124 5-methyl-1H-tetrazol-1-yl phenyl Het¹cyclopropylmethyl 392 2.94 125 5-methyl-1H-tetrazol-1-yl phenyl Het¹undecafluorocyclohexyl 618 4.94 126 5-methyl-1H-tetrazol-1-yl phenylHet¹ {[(1R,2S,5R)-5-methyl-2- 506 5.95 (propan-2-yl)cyclohexyl]oxy}methyl 127 5-methyl-1H-tetrazol-1-yl phenyl Het¹3-(2,2-dichloroethenyl)-2,2- 500 4.73 dimethylcyclopropyl 1285-methyl-1H-tetrazol-1-yl phenyl Het¹ difluoro[(4- 510 4.49methylphenyl)sulfanyl]methyl 129 5-methyl-1H-tetrazol-1-yl phenyl Het¹difluoro(3-methylphenoxy)methyl 494 4.31 130 5-methyl-1H-tetrazol-1-ylphenyl Het¹ 5-oxotetrahydrofuran-2-yl 422 2.44 1315-methyl-1H-tetrazol-1-yl phenyl Het¹ difluoro(4-methylphenoxy)methyl494 4.31 132 5-methyl-1H-tetrazol-1-yl phenyl Het¹ 4-ethoxyphenyl 4583.78 133 5-methyl-1H-tetrazol-1-yl phenyl Het¹tricyclo[3.3.1.1^(3,7)]dec-1-ylmethyl 486 5 1345-methyl-1H-tetrazol-1-yl phenyl Het¹ (1S,3R,5R,7S)- 486 5tricyclo[3.3.1.1^(3,7)]dec-1-ylmethyl 135 5-methyl-1H-tetrazol-1-ylphenyl Het¹ bicyclo[2.2.1]hept-2-ylmethyl 446 4.26 1365-methyl-1H-tetrazol-1-yl phenyl Het¹ [5-methyl-3-(trifluoromethyl)-1H-500 3.53 pyrazol-1-yl]methyl 137 5-methyl-1H-tetrazol-1-yl phenyl Het¹(2-methoxyethoxy)methyl 426 2.69 138 5-methyl-1H-tetrazol-1-yl phenylHet¹ 4-fluoro-2-(trifluoromethyl)phenyl 500 4.01 1395-methyl-1H-tetrazol-1-yl phenyl Het¹ tetrahydro-2H-pyran-2-yl 422 3.48140 5-methyl-1H-tetrazol-1-yl phenyl Het¹ (2-chlorophenoxy)methyl 4783.92 141 5-methyl-1H-tetrazol-1-yl phenyl Het¹ [2-(2- 470 2.59methoxyethoxy)ethoxy]methyl 142 5-methyl-1H-tetrazol-1-yl phenyl Het¹3-ethoxy-3-oxopropyl 438 2.92 143 5-methyl-1H-tetrazol-1-yl phenyl Het¹4-butylphenyl 470 4.84 144 5-methyl-1H-tetrazol-1-yl phenyl Het¹(benzyloxy)methyl 458 3.73 145 5-methyl-1H-tetrazol-1-yl phenyl Het¹5-methoxy-5-oxopentyl 452 2.86 146 5-methyl-1H-tetrazol-1-yl phenyl Het¹(3-chlorophenoxy)methyl 478 3.89 147 5-methyl-1H-tetrazol-1-yl phenylHet¹ 4-propylphenyl 456 4.49 148 5-methyl-1H-tetrazol-1-yl phenyl Het¹4-ethoxy-4-oxobutyl 452 2.98 149 5-methyl-1H-tetrazol-1-yl phenyl Het¹(4-chlorophenoxy)methyl 478 3.96 150 5-methyl-1H-tetrazol-1-yl phenylHet¹ 1,2,2,2-tetrafluoro-1- 622 4.92 (heptafluoropropoxy)ethyl 1515-methyl-1H-tetrazol-1-yl phenyl Het¹ (benzylsulfanyl)methyl 474 3.73152 5-methyl-1H-tetrazol-1-yl phenyl Het¹ 3-(4-chloro-2- 520 4.62methylphenoxy)propyl 153 5-methyl-1H-tetrazol-1-yl phenyl Het¹3-phenoxypropyl 472 3.78 154 1-methyl-1H-tetrazol-5-yl 3-fluorophenylHet² 4-propylphenyl 480 4.41 155 1-methyl-1H-tetrazol-5-yl3-fluorophenyl Het² 1-phenylcyclopropyl 478 4.01 1561-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² (E)-2-phenylethenyl 4643.69 157 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het²2-phenylcyclopropyl 478 3.85 158 1-methyl-1H-tetrazol-5-yl3-fluorophenyl Het² 2-(5-chlorothiophen-2-yl)ethyl 506 3.94 1591-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² 3-chlorophenyl 472 3.87160 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² 3-fluorophenyl 4563.53 161 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het²tridecafluorohexyl 680 4.81 162 1-methyl-1H-tetrazol-5-yl 3-fluorophenylHet² -4-[(2R,3aR,5S,6aS)-hexahydro- 482 4.262,5-methanopentalen-3a(1H)-yl 163 1-methyl-1H-tetrazol-5-yl3-fluorophenyl Het² bicyclo[2.2.1]hept-5-en-2-yl 454 3.48 1641-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² pentadecafluoroheptyl 730** 5.17 165 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het²2-fluoro-3-(trifluoromethyl)phenyl 524 3.89 1661-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² 4-ethylphenyl 466 4.04 1671-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² 6-chloropyridin-3-yl 4733.23 168 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² thiophen-2-yl 4443.27 169 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het²cyclohex-3-en-1-yl 442 3.48 170 1-methyl-1H-tetrazol-5-yl 3-fluorophenylHet² cyclopropylmethyl 416 2.98 171 1-methyl-1H-tetrazol-5-yl3-fluorophenyl Het² undecafluorocyclohexyl 642 4.51 1721-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² {[(1R,2S,5R)-5-methyl-2-530 5.47 (propan-2- yl)cyclohexyl]oxy}methyl 1731-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² 1,1,2,2,3,3,4,4,5,5,6,6-662 4.24 dodecafluorohexyl 174 1-methyl-1H-tetrazol-5-yl 3-fluorophenylHet² 3-(2,2-dichloroethenyl)-2,2- 524 4.7 dimethylcyclopropyl 1751-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² difluoro[(4- 534 4.26methylphenyl)sulfanyl]methyl 176 1-methyl-1H-tetrazol-5-yl3-fluorophenyl Het² difluoro(3-methylphenoxy)methyl  518** 4.14 1771-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² 2,2-dichloro-1-ethyl-3-512 4.14 methylcyclopropyl 178 1-methyl-1H-tetrazol-5-yl 3-fluorophenylHet² difluoro(4-methylphenoxy)methyl 518 4.19 1791-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² 4-ethoxyphenyl  482** 3.8180 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het²tricyclo[3.3.1.1^(3,7)]dec-1-ylmethyl  510** 4.84 1811-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² (1S,3R,5R,7S)- 510 4.84tricyclo[3.3.1.1^(3,7)]dec-1-ylmethyl 182 1-methyl-1H-tetrazol-5-yl3-fluorophenyl Het² bicyclo[2.2.1]hept-2-ylmethyl  470** 4.16 1831-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² (2-methoxyethoxy)methyl450 2.68 184 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het²4-fluoro-2-(trifluoromethyl)phenyl 524 3.92 1851-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² tetrahydro-2H-pyran-2-yl446 3.27 186 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² [2-(2- 4942.66 methoxyethoxy)ethoxy]methyl 187 1-methyl-1H-tetrazol-5-yl3-fluorophenyl Het² prop-2-en-1-yl 402 2.84 1881-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² 3-ethoxy-3-oxopropyl 4622.9 189 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het²(3-chlorophenoxy)methyl 502 3.8 190 1-methyl-1H-tetrazol-5-yl3-fluorophenyl Het² 4-ethoxy-4-oxobutyl  476** 3.04 1911-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² (4-chlorophenoxy)methyl 502** 3.82 192 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het²heptafluoropropyl  530** 3.75 193 1-methyl-1H-tetrazol-5-yl3-fluorophenyl Het² 1,2,2,2-tetrafluoro-1-  646** 4.54(heptafluoropropoxy)ethyl 194 1-methyl-1H-tetrazol-5-yl 3-fluorophenylHet² (benzylsulfanyl)methyl 498 3.68 195 1-methyl-1H-tetrazol-5-yl3-fluorophenyl Het² 3-(4-chloro-2-  544** 4.46 methylphenoxy)propyl 1961-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² 3-phenoxypropyl  496** 3.7197 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het²(1,1,1-trichloro-2-methylpropan-  536** 4.51 2-yl)oxy 1981-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² 4-(acetyloxy)butoxy  492**3.15 199 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² (1,7,7-trimethyl- 514** 5.05 bicyclo[2,2,1]hept-2-yl)oxy 200 1-methyl-1H-tetrazol-5-yl3-fluorophenyl Het² but-3-en-1-yloxy 432 3.37 2011-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² 2,2,2-trichloroethoxy 5083.85 202 1-methyl-1H-tetrazol-5-yl phenyl Het² 2-(benzyloxy)ethoxy 3.53203 1-methyl-1H-tetrazol-5-yl phenyl Het² pent-4-yn-1-yloxy 410 2.9 2041-methyl-1H-tetrazol-5-yl phenyl Het² thiophen-2-ylmethyl 440 3.09 2051-methyl-1H-tetrazol-5-yl phenyl Het² cyclohexylmethyl 440 3.89 2061-methyl-1H-tetrazol-5-yl phenyl Het² 2-cyclohexylethyl 454 4.3 2071-methyl-1H-tetrazol-5-yl phenyl Het² 2-cyclopentylethyl 440 3.99 2081-methyl-1H-tetrazol-5-yl phenyl Het² phenoxymethyl 450 3.31 2091-methyl-1H-tetrazol-5-yl phenyl Het¹ thiophen-2-ylmethyl 434 3.23 2101-methyl-1H-tetrazol-5-yl phenyl Het² difluoro(phenylsulfanyl)methyl3.85 211 1-methyl-1H-tetrazol-5-yl phenyl Het² 3-cyclohexylpropyl 4684.73 212 1-methyl-1H-tetrazol-5-yl phenyl Het¹ 3-chlorophenyl 448 3.85213 1-methyl-1H-tetrazol-5-yl phenyl Het¹ 3-fluorophenyl 432 3.48 2141-methyl-1H-tetrazol-5-yl phenyl Het¹ thiophen-2-yl 420 3.21 2151-methyl-1H-tetrazol-5-yl phenyl Het¹ 4-butylphenyl 470 4.78 2161-methyl-1H-tetrazol-5-yl phenyl Het¹ 4-ethylphenyl 442 3.99 2171-methyl-1H-tetrazol-5-yl phenyl Het¹ 3-phenoxypropyl 472 3.69 2181-methyl-1H-tetrazol-5-yl phenyl Het¹ (benzylsulfanyl)methyl 474 3.73219 1-methyl-1H-tetrazol-5-yl phenyl Het¹ 5-(acetylsulfanyl)pentyl 4823.55 220 1-methyl-1H-tetrazol-5-yl phenyl Het¹2-(tetrahydrofuran-2-yl)ethyl 436 2.77 221 1-methyl-1H-tetrazol-5-ylphenyl Het¹ 3-(thiophen-3-yl)propyl 462 3.7 2225-methyl-1H-tetrazol-1-yl phenyl Het² thiophen-2-ylmethyl 440 3.13 2235-methyl-1H-tetrazol-1-yl phenyl Het² cyclohexylmethyl 440 3.96 2245-methyl-1H-tetrazol-1-yl phenyl Het² 2-cyclohexylethyl 454 4.41 2255-methyl-1H-tetrazol-1-yl phenyl Het² 2-cyclopentylethyl 440 4.06 2265-methyl-1H-tetrazol-1-yl phenyl Het² phenoxymethyl 450 3.37 2275-methyl-1H-tetrazol-1-yl phenyl Het² difluoro(phenylsulfanyl)methyl 5023.89 228 5-methyl-1H-tetrazol-1-yl phenyl Het² difluoro(phenoxy)methyl486 3.78 229 5-methyl-1H-tetrazol-1-yl phenyl Het² 3-cyclohexylpropyl468 4.82 230 5-methyl-1H-tetrazol-1-yl phenyl Het² 2-(benzyloxy)ethoxy494 3.58 231 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² phenylethynyl462 3.71 232 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het²(Z)-2-chloro-2-phenylethenyl 498 3.89 233 1-methyl-1H-tetrazol-5-yl3-fluorophenyl Het² thiophen-3-ylmethyl 458 3.21 2341-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² pent-4-yn-1-yl 428 3.02235 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² cyclohexylmethyl 4584.01 236 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² 2-cyclohexylethyl472 4.44 237 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het²2-cyclopentylethyl 458 4.11 238 1-methyl-1H-tetrazol-5-yl 3-fluorophenylHet² phenoxymethyl 468 3.42 239 1-methyl-1H-tetrazol-5-yl 3-fluorophenylHet² difluoro(phenylsulfanyl)methyl 520 3.94 2401-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² difluoro(phenoxy)methyl504 3.83 241 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het²3-cyclohexylpropyl 486 4.84 242 1-methyl-1H-tetrazol-5-yl phenyl Het¹1-(4-bromophenoxy)ethyl 536 4.21 243 1-methyl-1H-tetrazol-5-yl phenylHet² 3-(2,2-dichloroethenyl)-2,2- 506 4.44 dimethylcyclopropyl 2441-methyl-1H-tetrazol-5-yl phenyl Het² (1,1,1-trichloro-2-methylpropan-518 4.36 2-yl)oxy 245 1-methyl-1H-tetrazol-5-yl phenyl Het²2,2,2-trichloroethoxy 490 3.7 246 1-methyl-1H-tetrazol-5-yl phenyl Het²(2,4-dichlorophenoxy)methyl 518 4.06 247 1-methyl-1H-tetrazol-5-ylphenyl Het² (2-chlorophenoxy)methyl 484 3.61 2481-methyl-1H-tetrazol-5-yl phenyl Het² 3-chlorophenyl 454 3.73 2491-methyl-1H-tetrazol-5-yl phenyl Het² (3-chlorophenoxy)methyl 484 3.7250 1-methyl-1H-tetrazol-5-yl phenyl Het² (4-chlorophenoxy)methyl 4843.68 251 1-methyl-1H-tetrazol-5-yl phenyl Het² 6-chloropyridin-3-yl 4553.09 252 1-methyl-1H-tetrazol-5-yl phenyl Het²2-(5-chlorothiophen-2-yl)ethyl 488 3.82 253 1-methyl-1H-tetrazol-5-ylphenyl Het² pentadecafluoroheptyl 712 5.08 254 1-methyl-1H-tetrazol-5-ylphenyl Het² 1,2,2,2-tetrafluoro-1- 628 4.46 (heptafluoropropoxy)ethyl255 1-methyl-1H-tetrazol-5-yl phenyl Het²4-fluoro-2-(trifluoromethyl)phenyl 506 3.78 2561-methyl-1H-tetrazol-5-yl phenyl Het² [5-methyl-3-(trifluoromethyl)-1H-506 3.33 pyrazol-1-yl]methyl 257 1-methyl-1H-tetrazol-5-yl phenyl Het²difluoro(3-methylphenoxy)methyl 500 4.04 258 1-methyl-1H-tetrazol-5-ylphenyl Het² difluoro(4-methylphenoxy)methyl 500 4.06 2591-methyl-1H-tetrazol-5-yl phenyl Het² difluoro[(4- 516 4.16methylphenyl)sulfanyl]methyl 260 1-methyl-1H-tetrazol-5-yl phenyl Het²undecafluorocyclohexyl 624 4.44 261 1-methyl-1H-tetrazol-5-yl phenylHet² 3-fluorophenyl 438 3.39 262 1-methyl-1H-tetrazol-5-yl phenyl Het¹1-(4-fluorophenoxy)ethyl 476 3.79 263 1-methyl-1H-tetrazol-5-yl phenylHet² (4-iodophenoxy)methyl 576 3.94 264 1-methyl-1H-tetrazol-5-yl phenylHet¹ but-3-yn-1-yloxy 406 3.09 265 5-methyl-1H-tetrazol-1-yl phenyl Het¹prop-2-en-1-yloxy 394 3.27 266 1-methyl-1H-tetrazol-5-yl phenyl Het²-4-[(2R,3aR,5S,6aS)-hexahydro- 464 4.14 2,5-methanopentalen-3a(1H)-yl267 1-methyl-1H-tetrazol-5-yl phenyl Het² 1-phenylcyclopropyl 460 3.87268 1-methyl-1H-tetrazol-5-yl phenyl Het² 4-butylphenyl 476 4.68 2691-methyl-1H-tetrazol-5-yl phenyl Het² 4-propylphenyl 462 4.29 2701-methyl-1H-tetrazol-5-yl phenyl Het² 4-ethylphenyl 448 3.92 2711-methyl-1H-tetrazol-5-yl phenyl Het² 4-ethoxyphenyl 464 3.64 2721-methyl-1H-tetrazol-5-yl phenyl Het² thiophen-2-yl 426 3.13 2731-methyl-1H-tetrazol-5-yl phenyl Het² bicyclo[2.2.1]hept-5-en-2-yl 4363.33 274 1-methyl-1H-tetrazol-5-yl phenyl Het² 2-phenylcyclopropyl 4603.71 275 1-methyl-1H-tetrazol-5-yl phenyl Het² cyclohex-3-en-1-yl 4243.35 276 1-methyl-1H-tetrazol-5-yl phenyl Het² 5-oxotetrahydrofuran-2-yl428 2.26 277 1-methyl-1H-tetrazol-5-yl phenyl Het² 1-phenoxyethyl 4643.53 278 1-methyl-1H-tetrazol-5-yl phenyl Het² (1S,3R,5R,7S)- 492 4.69tricyclo[3.3.1.1^(3,7)]dec-1-ylmethyl 279 1-methyl-1H-tetrazol-5-ylphenyl Het² tricyclo[3.3.1.1^(3,7)]dec-1-ylmethyl 492 4.69 2801-methyl-1H-tetrazol-5-yl phenyl Het² bicyclo[2.2.1]hept-2-ylmethyl 4524.01 281 1-methyl-1H-tetrazol-5-yl phenyl Het² cyclopropylmethyl 3982.84 282 1-methyl-1H-tetrazol-5-yl phenyl Het² 3-ethoxy-3-oxopropyl 4442.73 283 1-methyl-1H-tetrazol-5-yl phenyl Het² 4-ethoxy-4-oxobutyl 4582.9 284 1-methyl-1H-tetrazol-5-yl phenyl Het² {[(1R,2S,5R)-5-methyl-2-512 5.39 (propan-2- yl)cyclohexyl]oxy}methyl 2851-methyl-1H-tetrazol-5-yl phenyl Het² [2-(2-methoxy- 476 2.51ethoxy)ethoxy]methyl 286 1-methyl-1H-tetrazol-5-yl phenyl Het²(2-methoxyethoxy)methyl 432 2.54 287 1-methyl-1H-tetrazol-5-yl phenylHet² (1,7,7-trimethylbicyclo[2.2.1] 496 4.92 hept-2-yl)oxy 2881-methyl-1H-tetrazol-5-yl phenyl Het² 4-(acetyloxy)butoxy 474 3 2891-methyl-1H-tetrazol-5-yl phenyl Het² (biphenyl-2-yloxy)methyl 526 4.32290 1-methyl-1H-tetrazol-5-yl phenyl Het² but-2-yn-1-yloxy 412 3.04 2915-methyl-1H-tetrazol-1-yl phenyl Het² (benzyloxy)methyl 464 3.46 2925-methyl-1H-tetrazol-1-yl 3-fluorophenyl Het² but-3-yn-1-yloxy 430 3.02293 5-methyl-1H-tetrazol-1-yl 3-fluorophenyl Het² but-2-yn-1-yloxy 4303.17 294 5-methyl-1H-tetrazol-1-yl 3-fluorophenyl Het² 2-fluoroethoxy424 2.77 295 5-methyl-1H-tetrazol-1-yl 3-fluorophenyl Het²but-3-en-1-yloxy 432 3.39 296 1-methyl-1H-tetrazol-5-yl 3-fluorophenylHet² 1-methylcyclohexyl 458 4.16 297 1-methyl-1H-tetrazol-5-yl3-fluorophenyl Het² 4-butylphenyl 494 4.81 298 1-methyl-1H-tetrazol-5-yl3-fluorophenyl Het² 5-methoxy-5-oxopentyl 476 2.94 2991-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² 2-ethoxyethyl  434** 2.78300 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² 3-methoxybutoxy 4643.13 301 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het² 2-methoxyethoxy436 2.66 302 5-methyl-1H-tetrazol-1-yl phenyl Het¹ 2-fluoroethoxy 4002.84 303 1-methyl-1H-tetrazol-5-yl 2-methylphenyl Het¹ 2-cyclohexylethyl462 4.73 304 1-methyl-1H-tetrazol-5-yl 2-methylphenyl Het¹2-phenoxyethyl 472 3.67 305 1-methyl-1H-tetrazol-5-yl 2-chlorophenylHet¹ 2-cyclohexylethyl 482 4.7 306 1-methyl-1H-tetrazol-5-yl phenyl Het¹4-methylphenyl 428 3.65 307 1-methyl-1H-tetrazol-5-yl phenyl Het¹2-methylphenyl 428 3.5 308 1-methyl-1H-tetrazol-5-yl phenyl Het¹4-fluorophenyl 432 3.46 309 1-methyl-1H-tetrazol-5-yl phenyl Het¹2-fluorophenyl 431 3.52 310 1-methyl-1H-tetrazol-5-yl phenyl Het¹4-chlorophenyl 3.83 311 1-methyl-1H-tetrazol-5-yl phenyl Het¹2-chlorophenyl 448 3.44 312 1-methyl-1H-tetrazol-5-yl phenyl Het¹3-methoxyphenyl 444 3.44 313 1-methyl-1H-tetrazol-5-yl phenyl Het¹3-ethoxyphenyl 458 3.79 314 1-methyl-1H-tetrazol-5-yl phenyl Het¹2-chloropyridin-3-yl 2.82 315 1-methyl-1H-tetrazol-5-yl 2-methylphenylHet¹ but-3-en-1-yloxy 422 3.65 316 1-methyl-1H-tetrazol-5-yl2-methylphenyl Het¹ but-3-yn-1-yloxy 420 3.23 3171-methyl-1H-tetrazol-5-yl phenyl Het² 489 3.83 3181-methyl-1H-tetrazol-5-yl phenyl Het² 3-(trifluoromethyl)phenyl 488 3.92319 1-methyl-1H-tetrazol-5-yl phenyl Het² 2-phenoxyphenyl 512 4.36 3201-methyl-1H-tetrazol-5-yl phenyl Het² quinolin-2-yl 471 4.04 3211-methyl-1H-tetrazol-5-yl phenyl Het² 2,4-difluorophenyl 456 3.37 3221-methyl-1H-tetrazol-5-yl phenyl Het² 2-methoxyphenyl 450 3.5 3231-methyl-1H-tetrazol-5-yl phenyl Het² 3,5-dichlorophenyl 488 4.36 3241-methyl-1H-tetrazol-5-yl phenyl Het² 3-iodophenyl 546 4.01 3251-methyl-1H-tetrazol-5-yl phenyl Het² 2-(trifluoromethoxy)phenyl 5043.61 326 1-methyl-1H-tetrazol-5-yl phenyl Het² 4-fluorophenyl 438 3.39327 1-methyl-1H-tetrazol-5-yl phenyl Het² 2-methylphenyl 434 3.41 3281-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹ 2-(trifluoromethoxy)phenyl516 3.9 329 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹ 4-fluorophenyl450 3.57 330 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹4-phenoxyphenyl 524 4.51 331 1-methyl-1H-tetrazol-5-yl 3-fluorophenylHet¹ 2-methylphenyl 446 3.61 332 1-methyl-1H-tetrazol-5-yl phenyl Het²2-chloropyridin-3-yl 455 2.73 333 1-methyl-1H-tetrazol-5-yl phenyl Het²4-chlorophenyl 454 3.74 334 1-methyl-1H-tetrazol-5-yl phenyl Het²2-chlorophenyl 454 3.29 335 1-methyl-1H-tetrazol-5-yl phenyl Het²4-methylphenyl 434 3.59 336 1-methyl-1H-tetrazol-5-yl phenyl Het²2,4-dichlorophenyl 488 3.76 337 1-methyl-1H-tetrazol-5-yl phenyl Het²2-bromophenyl 498 3.33 338 1-methyl-1H-tetrazol-5-yl phenyl Het²2-fluorophenyl 438 3.27 339 1-methyl-1H-tetrazol-5-yl phenyl Het² 4723.96 340 1-methyl-1H-tetrazol-5-yl phenyl Het² 3,5-difluorophenyl 4563.63 341 1-methyl-1H-tetrazol-5-yl phenyl Het²3-fluoro-5-(trifluoromethyl)phenyl 506 4.11 3421-methyl-1H-tetrazol-5-yl phenyl Het² 502 3.81 3431-methyl-1H-tetrazol-5-yl phenyl Het² 518 4.16 3441-methyl-1H-tetrazol-5-yl phenyl Het² 3-bromophenyl 3.85 3451-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹ 2-methoxyphenyl 462 3.79346 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹ 3,5-dichlorophenyl 5004.61 347 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹ 3-iodophenyl 5584.21 348 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹3-fluoro-5-(trifluoromethyl)phenyl 518 4.34 3491-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹ 3-propoxyphenyl 490 4.31350 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹ 3-methoxy-5- 530 4.59(trifluoromethyl)phenyl 351 1-methyl-1H-tetrazol-5-yl 3-fluorophenylHet¹ 514 3.99 352 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹ 530 4.31353 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹ 3-bromophenyl 510 4.06354 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹2-chloro-4-methylphenyl 480 3.9 355 1-methyl-1H-tetrazol-5-yl3-fluorophenyl Het¹ 501 4.06 356 1-methyl-1H-tetrazol-5-yl3-fluorophenyl Het¹ 3-(trifluoromethyl)phenyl 500 4.11 3571-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹ 3-phenoxyphenyl 524 4.51358 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹ furan-2-yl 422 3.04359 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹ 2,4-difluorophenyl 4683.76 360 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹2-chloropyridin-3-yl 467 2.94 361 1-methyl-1H-tetrazol-5-yl3-fluorophenyl Het¹ 4-chlorophenyl 466 3.94 3621-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹ 2-chlorophenyl 466 3.57363 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹ 4-methylphenyl 4463.76 364 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹2,4-dichlorophenyl 500 4.04 365 1-methyl-1H-tetrazol-5-yl 3-fluorophenylHet¹ 2-bromophenyl 510 3.59 366 1-methyl-1H-tetrazol-5-yl 3-fluorophenylHet¹ 2-fluorophenyl 450 3.65 367 1-methyl-1H-tetrazol-5-yl3-fluorophenyl Het¹ 484 4.19 368 1-methyl-1H-tetrazol-5-yl3-fluorophenyl Het¹ 3,5-difluorophenyl 468 3.83 3691-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹ 3-ethoxyphenyl 476 3.87370 1-methyl-1H-tetrazol-5-yl 3-fluorophenyl Het¹ 3-methoxyphenyl 4623.55 371 1-methyl-1H-tetrazol-5-yl 2-methylphenyl Het¹ 4-methylphenyl442 3.81 372 1-methyl-1H-tetrazol-5-yl 2-chlorophenyl Het¹but-3-yn-1-yloxy 440 3.21 373 1-methyl-1H-tetrazol-5-yl 2-chlorophenylHet¹ 2-phenoxyethyl 492 3.63 374 1-methyl-1H-tetrazol-5-yl3-fluorophenyl Het¹ but-3-yn-1-yloxy 424 3.21 3751-methyl-1H-tetrazol-5-yl phenyl Het¹ difluoro(phenoxy)methyl 480 3.94376 1-methyl-1H-tetrazol-5-yl phenyl Het² but-3-yn-1-yloxy 412 2.88 3771-methyl-1H-tetrazol-5-yl phenyl Het¹ but-3-yn-1-yloxy 406 3.09 3781-methyl-1H-tetrazol-5-yl phenyl Het² phenoxymethyl 450 3.33 3791-methyl-1H-tetrazol-5-yl phenyl Het² phenoxymethyl 450 3.13 Measurementof logP values was performed according EEC directive 79/831 Annex V.A8by HPLC (High Performance Liquid Chromatography) on reversed phasecolumns with the following methods: measurement of LC-MS was done at pH2.7 with 0.1% formic acid in water and with acetonitrile (contains 0.1%formic acid) as eluent with a linear gradient from 10% acetonitrle to95% acetonitrile. Calibration was done with not branched alkan2-ones(with 3 to 16 carbon atoms) with known logP-values (measurement of logPvalues using retention times with linear interpolation betweensuccessive alkanones). lambda-maX-values were determined usingUV-spectra from 200 nm to 400 nm and the peak values of thechromatographic signals. In table 1, M + H (or M H) means the molecularion peak, plus or minus 1 a.m.u. (atomic mass unit) respectively, asobserved in mass spectroscopy and M (Apcl+) means the molecular ion peakas it was found via positive atmospheric pressure chemical ionisation inmass spectroscopy Molecular Weight measurement, Method: **LCT-ESI*SQD-ESI

In the following list we specify the double bond geometry of theexamples of table 1 as shown here:

Example (Double Bond Geometry) of the Examples of Table 1:1 (E), 2 (E), 3 (U), 4 (U), 5 (U), 6 (U), 7 (U), 8 (U), 9 (U), 10 (U),11 (U), 12 (U), 13 (U), 14 (U), (U), 16 (U), 17 (U), 18 (U), 19 (U), 20(U), 21 (U), 22 (U), 23 (U), 24 (U), 25 (U), 26 (U), 27 (U), 28 (U), 29(U), 30 (U), 31 (U), 32 (U), 33 (U), 34 (U), 35 (U), 36 (U), 37 (U), 38(U), 39 (U), 40 (U), 41 (U), 42 (U), 43 (U), 44 (U), 45 (U), 46 (U), 47(U), 48 (U), 49 (Z), 50 (Z), 51 (Z), 52 (Z), 53 (Z), 54 (Z), 55 (Z), 56(Z), 57 (Z), 58 (Z), 59 (Z), 60 (Z), 61 (Z), 62 (Z), 63 (Z), 64 (Z), 65(Z), 66 (Z), 67 (Z), 68 (Z), 69 (U), 70 (U), 71 (U), 72 (U), 73 (U), 74(U), 75 (U), 76 (U), 77 (U), 78 (U), 79 (U), 80 (U), 81 (U), 82 (U), 83(U), 84 (U), 85 (U), 86 (U), 87 (U), 88 (U), 89 (U), 90 (U), 91 (U), 92(U), 93 (U), 94 (U), 95 (U), 96 (U), 97 (U), 98 (U), 99 (U), 100 (U),101 (U), 102 (U), 103 (U), 104 (U), 105 (U), 106 (U), 107 (U), 108 (U),109 (U), 110 (U), 111 (U), 112 (U), 113 (U), 114 (U), 115 (U), 116 (U),117 (U), 118 (U), 119 (U), 120 (U), 121 (U), 122 (U), 123 (U), 124 (U),125 (U), 126 (U), 127 (U), 128 (U), 129 (U), 130 (U), 131 (U), 132 (U),133 (U), 134 (U), 135 (U), 136 (U), 137 (U), 138 (U), 139 (U), 140 (U),141 (U), 142 (U), 143 (U), 144 (U), 145 (U), 146 (U), 147 (U), 148 (U),149 (U), 150 (U), 151 (U), 152 (U), 153 (U), 154 (Z), 155 (Z), 156 (Z),157 (Z), 158 (Z), 159 (Z), 160 (Z), 161 (Z), 162 (Z), 163 (Z), 164 (Z),165 (Z), 166 (Z), 167 (Z), 168 (Z), 169 (Z), 170 (Z), 171 (Z), 172 (Z),173 (Z), 174 (Z), 175 (Z), 176 (Z), 177 (Z), 178 (Z), 179 (Z), 180 (Z),181 (Z), 182 (Z), 183 (Z), 184 (Z), 185 (Z), 186 (Z), 187 (Z), 188 (Z),189 (Z), 190 (Z), 191 (Z), 192 (Z), 193 (Z), 194 (Z), 195 (Z), 196 (Z),197 (Z), 198 (Z), 199 (Z), 200 (Z), 201 (Z), 202 (Z), 203 (Z), 204 (Z),205 (Z), 206 (Z), 207 (Z), 208 (U), 209 (Z), 210 (U), 211 (Z), 212 (Z),213 (Z), 214 (Z), 215 (Z), 216 (Z), 217 (Z), 218 (Z), 219 (U), 220 (U),221 (U), 222 (U), 223 (U), 224 (U), 225 (U), 226 (U), 227 (U), 228 (U),229 (U), 230 (U), 231 (Z), 232 (Z), 233 (Z), 234 (Z), 235 (Z), 236 (Z),237 (Z), 238 (Z), 239 (Z), 240 (Z), 241 (Z), 242 (U), 243 (Z), 244 (Z),245 (Z), 246 (U), 247 (Z), 248 (Z), 249 (Z), 250 (Z), 251 (Z), 252 (Z),253 (Z), 254 (Z), 255 (Z), 256 (Z), 257 (Z), 258 (Z), 259 (Z), 260 (Z),261 (Z), 262 (U), 263 (U), 264 (U), 265 (U), 266 (Z), 267 (Z), 268 (Z),269 (Z), 270 (Z), 271 (Z), 272 (Z), 273 (Z), 274 (Z), 275 (Z), 276 (Z),277 (Z), 278 (Z), 279 (Z), 280 (Z), 281 (Z), 282 (Z), 283 (Z), 284 (Z),285 (Z), 286 (Z), 287 (Z), 288 (Z), 289 (U), 290 (U), 291 (U), 292 (U),293 (U), 294 (U), 295 (U), 296 (Z), 297 (Z), 298 (Z), 299 (Z), 300 (Z),301 (Z), 302 (U), 303 (U), 304 (U), 305 (U), 306 (Z), 307 (Z), 308 (Z),309 (Z), 310 (Z), 311 (Z), 312 (Z), 313 (Z), 314 (Z), 315 (U), 316 (U),317 (Z), 318 (Z), 319 (Z), 320 (Z), 321 (Z), 322 (Z), 323 (Z), 324 (Z),325 (Z), 326 (Z), 327 (Z), 328 (Z), 329 (Z), 330 (Z), 331 (Z), 332 (Z),333 (Z), 334 (Z), 335 (Z), 336 (Z), 337 (Z), 338 (Z), 339 (Z), 340 (Z),341 (Z), 342 (Z), 343 (Z), 344 (Z), 345 (Z), 346 (Z), 347 (Z), 348 (Z),349 (Z), 350 (Z), 351 (Z), 352 (Z), 353 (Z), 354 (Z), 355 (Z), 356 (Z),357 (Z), 358 (Z), 359 (Z), 360 (Z), 361 (Z), 362 (Z), 363 (Z), 364 (Z),365 (Z), 366 (Z), 367 (Z), 368 (Z), 369 (Z), 370 (Z), 371 (U), 372 (U),373 (U), 374 (Z), 375 (Z), 376 (Z), 377 (Z), 378 (Z), 379 (E),

EXAMPLE A Phytophthora Test (Tomato)/Preventive

Solvent: 49 parts by weight of N,N-Dimethylformamide

Emulsifier: 1 part by weight of Alkylarylpolyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound at the stated rate of application. Oneday after this treatment, the plants are inoculated with an aqueousspore suspension of Phytophthora infestans. The plants remain for oneday in an incubation cabinet at approximately 22° C. and a relativeatmospheric humidity of 100%. Then the plants are placed in anincubation cabinet at approximately 20° C. and a relative atmospherichumidity of 96%.

The test is evaluated 7 days after the inoculation. 0% means an efficacywhich corresponds to that of the control, while an efficacy of 100%means that no disease is observed.

In this test the following examples of table 1 according to theinvention showed efficacy of 70% or even higher at a concentration of500 ppm of active ingredient:

Examples Number 1, 2, 3, 4, 5, 6, 7, 17, 18, 19, 20, 21, 22, 23, 24, 25,26, 27, 28, 29, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62,63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 74, 75, 76, 78, 80, 83, 84, 90,91, 92, 93, 94, 96, 98, 99, 100, 102, 103, 104, 105, 106, 109, 110, 112,113, 114, 115, 116, 117, 118, 120, 121, 122, 123, 124, 125, 126, 127,129, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143,146, 148, 149, 151, 160, 165, 175, 176, 197, 198, 199, 200, 201, 202,204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 217,218, 219, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231,232, 233, 234, 235, 236, 237, 238, 239, 240, 241, 375, 376 and 377.

EXAMPLE B Plasmopara Test (Grapevines)/Protective

Solvent: 24.5 parts by weight of acetone

-   -   24.5 parts by weight of dimethylacetamide        Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated rate of application. Afterthe spray coating has dried on, the plants are inoculated with anaqueous spore suspension of Plasmopara viticola and then remain for 1day in an incubation cabinet at approximately 20° C. and a relativeatmospheric humidity of 100%. The plant is subsequently placed for 4days in a greenhouse at approximately 21° C. and a relative atmospherichumidity of approximately 90%. The plants are then misted and placed for1 day in an incubation cabinet.

The test is evaluated 6 days after the inoculation. 0% means an efficacywhich corresponds to that of the control, while an efficacy of 100%means that no disease is observed.

In this test the following examples of table 1 according to theinvention showed efficacy of 70% or even higher at a concentration of 10ppm of active ingredient:

Examples Number 1, 2, 3, 4, 5, 6, 7, 17, 18, 19, 20, 23, 24, 27, 49, 50,51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 67, 70, 71,76, 80, 82, 84, 114, 115, 116, 135, 160, 202, 205, 206, 207, 208, 209,212, 213, 214, 216, 218, 220, 221, 223, 226, 230, 233, 234, 237, 238,376 and 377.

EXAMPLE C In Vitro-Test for the Calculation of the ED50-Value withPythium aphanidermatum

Wells of 96-hole microtitre plates are filled with 100 of a solution ofthe test compound in methanol together with the emulsifier alkylarylpolyglycol ether. Thereafter, the solvent is evaporated in a hood. Atthe next step, into each well 2000 of liquid potato dextrose medium isgiven that has been amended with an appropriate concentration of sporesor mycelium suspension of the test fungus. The resulting concentrationsof the test compounds in the microtitre well are 50, 5, 0.5 and 0.05ppm. The resulting concentration of the emulsifier in all wells isconstantly 300 ppm.

With the aid of a photometer the extinction in all wells is measured atthe wavelength of 620 nm.

The microtiter plates are then transferred for 3-5 days onto a shaker at20° C. and 85% relative humidity.

At the end of the incubation time the growth of the test organisms ismeasured again photometrically at the wavelength of 620 nm. Thedifference between the two extinction values (taken before and afterincubation) is proportional to the growth of the test organism.

Based on the Δ extinction data from the different test concentrationsand that of the untreated test organism (control) a dose-response curveis calculated. The concentration that is necessary to give 50% growthinhibition is defined and reported as ED50-value (=Effective Dose thatcauses 50% growth inhibition) in ppm (=mg/l).

In this test the following examples of table 1 according to theinvention showed an ED50-value lower than 1 ppm: Examples Number 1, 2,3, 4, 5, 6, 7, 19, 20, 21, 22, 23, 24, 25, 27, 28, 29, 49, 50, 51, 52,53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 69, 71, 73, 77, 78, 80, 81, 82,83, 84, 86, 87, 89, 91, 92, 93, 97, 99, 101, 103, 106, 109, 110, 112,113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126,127, 129, 130, 131, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142,143, 145, 146, 148, 149, 150, 151, 160, 164, 165, 171, 175, 176, 197,198, 199, 200, 201, 202, 204, 205, 206, 207, 208, 209, 210, 211, 212,213, 214, 215, 216, 217, 218, 221, 224, 227, 228, 229, 230, 231, 232,233, 234, 235, 236, 237, 238, 239, 240, 241, 375, 376 and 377.

The following examples illustrate in a non-limiting manner thepreparation and efficacy of the compounds of formula (I) according tothe invention.

Preparation ofN-{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}hex-5-ynamide(Compound 34) according to process P2 Step 1: Preparation2-{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione

To a solution ofN-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (21.5 g,0.106 mol) in acetonitrile (638 mL) was added cesium carbonate (72.4 g,0.222 mol), potassium iodide (1.76 g, 0.011 mol) and then2-[6-(bromomethyl)pyridin-2-yl]-1H-isoindole-1,3(2H)-dione (35.23 g,0.111 mol), the white slurry was stirred at room temperature for fourhours at room temperature. Water (700 mL) was added, the precipitate wasfiltered off and washed with water until colourless, then dried in vacuoovernight to yield to of2-{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione[40.0 g; 86% of theory; HPLC/MS: m/z=440 (M+H); log P(HCOOH)=3.04].

Step 2: Preparation of6-[({[(1(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine

To a solution of2-{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione(119 g, 0.271 mol) in tetrahydrofuran (2610 mL) was added hydrazinehydrate (66.26 mL, 1.354 mol), the reaction mixture was stirred at roomtemperature for six hours at room temperature. The precipitate which hasformed was filtered off and washed with tetrahydrofuran, the filtratewas then concentrated in vacuo to produce an off-white solid which wasfurther purified by trituration in dichloromethane yielding to6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine[83.0 g; 94% of theory; HPLC/MS m/z=310 (M+H); log P(HCOOH)=1.14].

Step 3: Preparation ofN-{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}hex-5-ynamide

To a solution of6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine(251 mg, 0.81 mmol) in dichloromethane (10 mL) was added triethylamine(0.22 mL, 1.62 mmol), hex-5-ynoyl chloride (211 mg, 1.62 mmol). Thereaction mixture was stirred for 5 hours at room temperature,concentrated in vacuo, and then purified by silica gel chromatography toyield toN-{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}hex-5-ynamide[200 mg; 95% of purity; 58% of theory; HPLC/MS: m/z=404 (M+H); logP_((HCOOH))=2.98].

Preparation of 4-chlorobutyl{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate(Compound 67) according to process P3 Step 1: Preparation of2-(6-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}pyridin-2-yl)-1H-isoindole-1,3(2H)-dione

A suspension of N-hydroxyphthalimide (35.0 g, 214 mmol),2-[6-(bromomethyl)pyridin-2-yl]-1H-isoindole-1,3(2H)-dione (74.8 g, 236mmol), cesium carbonate (146.8 g, 450 mmol) and potassium iodide (1.78g, 10.7 mmol) in acetonitrile (350 mL) was stirred at room temperaturefor 18 h. Water (300 mL) was added, the precipitate was filtered off andwashed with water until colourless, then dried in vacuo overnight toyield2-(6-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}pyridin-2-yl)-1H-isoindole-1,3(2H)-dioneas a colourless solid [85.0 g; 94% of theory; HPLC/MS m/z=400 (M+H); logP(HCOOH)=2.44].

Step 2: Preparation of 6-[(aminooxy)methyl]pyridin-2-amine

To a solution of2-(6-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}pyridin-2-yl)-1H-isoindole-1,3(2H)-dione(50 g, 125 mmol) in THF (350 mL) was added dropwise hydrazine hydrate(61 mL, 1.25 mol) at room temperature. After stirring overnight at roomtemperature, the reaction mixture was filtered and the filtrate wasconcentrated to dryness in vacuo. Purification of the residue on silicagel afforded 6-[(aminooxy)methyl]pyridin-2-amine as a colourless oil[10.0 g; 57% of theory; HPLC/MS: m/z=140 (M+H); log P(HCOOH)<−0.23].

Step 3: Preparation of6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)-methyl]pyridin-2-amineby the condensation of 6-[(aminooxy)methyl]pyridin-2-amine with1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

Under protective gas (argon), a reaction tube containing a solution of(1-methyl-1H-tetrazol-5-yl)(phenyl)methanone (188 mg; 1.0 mmol),6-[(aminooxy)methyl]pyridin-2-amine (139 mg; 1.0 mmol) andp-toluenesulfonic acid monohydrate (190 mg; 1.0 mmol) in 2-propanol (2mL) is sealed and heated in a microwave oven at 160° C. for 90 min. Forworkup, the mixture is allowed to cool down, diluted withdichloromethane (10 mL) and washed twice with 3 ml each time of sat. aq.sodium bicarbonate. The aqueous phase is extracted with dichloromethaneand the combined organic layers dried over magnesium sulfate andconcentrated under reduced pressure. Purification on silica gel affords6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amineas a colourless oil [205 mg; 66% of theory; HPLC/MS: m/z=310 (M+H); logP_((HCOOH))=1.13].

Step 4: Preparation of 4-chlorobutyl{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate(Compound 67)

To a stirred solution of6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)-methyl]pyridin-2-amine(150 mg, 0.485 mmol) in dichloromethane (5 mL), was added pyridine(0.078 mL), 4-chlorobutyl carbonochloridate (166 mg, 0.970 mmol). Thereaction mixture was stirred for 5 hours at room temperature,concentrated in vacuo, and then purified by silica gel chromatography toyield to 4-chlorobutyl{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate[200 mg; 90% of purity; 84% of to theory; HPLC/MS: m/z=344 (M+H); logP_((HCOOH))=3.67].

Preparation of 4-[(aminooxy)methyl]-1,3-thiazol-2-amine Step 1:Preparation of2-[(2-amino-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione

A suspension of N-hydroxyphthalimide (50.0 g, 306 mmol),4-(chloromethyl)-1,3-thiazol-2-amine (50.1 g, 337 mmol), cesiumcarbonate (210 g, 0.64 mol) and potassium iodide (2.54 g, 15.3 mmol) inacetonitrile (440 mL) was stirred at room temperature for 18 h. Water(300 mL) was added, the precipitate was filtered off and washed withwater until colourless, then dried in vacuo overnight to afford2-[(2-amino-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione as acolourless solid [36.0 g; 43% of theory; HPLC/MS: m/z=276 (M+H); logP(HCOOH)=0.74].

Step 2: 4-[(aminooxy)methyl]-2-bromo-1,3-thiazole

To a solution of2-[(2-amino-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione (10 g,36.3 mmol) in THF (100 mL) was added dropwise hydrazine hydrate (9.1 g,181 mmol) at room temperature. After stirring overnight at roomtemperature, the reaction mixture was filtered and the filtrate wasconcentrated to dryness in vacuo. Purification of the residue on silicagel afforded 4-[(aminooxy)methyl]-2-bromo-1,3-thiazole as a colourlessoil [5.2 g; 99% of theory; HPLC/MS: m/z=146 (M+H); log P(HCOOH)<−0.23].

The invention claimed is:
 1. A compound of formula (I)

wherein: X is selected from the group consisting of a hydrogen atom, ahalogen atom, C₁-C₈-alkoxy, a cyano group, a methanesulfonyl group, anitro group, a trifluoromethyl group and an aryl group; A is a tetrazoylgroup of formula (A¹) or (A²):

wherein Y is substituted or non-substituted C₁-C₈; and Het is selectedfrom the group consisting of a pyridyl group of formula (Het¹) and athiazolyl group of formula (Het²);

wherein Q is selected from the group consisting of a substituted ornon-substituted tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl, substituted ornon-substituted tri(C₁-C₈-alkyl)silyl-C₃-C₈-cycloalkyl, substituted ornon-substituted aryl-cyclopropyl, substituted or non-substitutedC₃-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, substituted ornon-substituted C₃-C₈-cycloalkyl-C₁-C₈-alkyl, substituted ornon-substituted C₃-C₈-cycloalkenyl, substituted or non-substitutedC₃-C₈-cycloalkenyl-C₁-C₈-alkyl, a substituted or non-substitutedC₂-C₈-halogenoalkenyl having 1 to 5 halogen atoms, substituted ornon-substituted C₂-C₈-alkynyl, substituted or non-substitutedC₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms, substituted ornon-substituted C₁-C₈-halogenoalkoxyalkyl having 1 to 5 halogen atoms,substituted or non-substituted phenoxyalkyl, substituted ornon-substituted C₂-C₈-alkenyloxy, substituted or non-substitutedC₂-C₈-halogenoalkenyloxy having 1 to 5 halogen atoms, substituted ornon-substituted C₃-C₈-alkynyloxy, substituted or non-substitutedC₃-C₈-halogenoalkynyloxy having 1 to 5 halogen atoms, substituted ornon-substituted (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl, substituted ornon-substituted (C₁-C₈-alkenyloxyimino-C₁-C₈-alkyl, substituted ornon-substituted (C₁-C₈-alkynyloxyimino)-C₁-C₈-alkyl, substituted ornon-substituted (benzyloxyimino)-C₁-C₈-alkyl, substituted benzyloxy,substituted or non-substituted phenoxy, substituted aryl, substituted ornon-substituted, saturated or unsaturated 4-, 5-, 6- or 7-memberedheterocyclyl comprising up to 4 heteroatoms selected in the listconsisting of N, O, S; [substituted aryl]-[C₁-C₈]-alkyl; substituted ornon-substituted, saturated or unsaturated 4-, 5-, 6- or 7-memberedheterocyclyl-[C₁-C₈]-alkyl comprising up to 4 heteroatoms selected inthe list consisting of N, O, S; saturated or unsaturated 4-, 5-, 6- or7-membered heterocyclyl-[C₁-C₈]-halogenoalkyl comprising up to 4heteroatoms selected in the list consisting of N, O, S and having 1 to 5halogen atoms; substituted or non-substituted tri(C₁-C₈-alkyl)-silyloxy,substituted or non-substituted C₅-C₁₂-fused bicycloalkyl, substituted ornon-substituted C₅-C₁₂-fused bicycloalkenyl, substituted ornon-substituted C₅-C₁₂-fused bicycloalkyl-[C₁-C₈]-alkyl, substituted ornon-substituted C₅-C₁₂-fused bicycloalkenyl-[C₁-C₈]-alkyl, substitutedor non-substituted arylcarbonyl, substituted or non-substitutedC₁-C₈-alkylcarbonyl, and substituted or non-substituted, saturated orunsaturated 4-, 5-, 6- or 7-membered heterocyclylcarbonyl comprising upto 4 heteroatoms selected from the group consisting N, O, and S; as wellas salts, N-oxides, or (E) and (Z) isomers and mixtures thereof.
 2. Thecompound of claim 1 wherein X is selected from the group consisting of ahydrogen atom, a halogen atom, substituted or non-substitutedC₁-C₈-alkyl, a substituted or non-substituted C₁-C₈-alkoxy, a cyanogroup, a methanesulfonyl group, a nitro group, a trifluoromethyl groupand an aryl group.
 3. The compound of claim 2 wherein X is selected fromthe group consisting of a chlorine atom, a fluorine atom, a methylgroup, an ethyl group, an n-propyl group, an isopropyl group, an n-butylgroup, an isobutyl group, a sec-butyl group, a tert-butyl group, amethoxy group, an ethoxy group, a propoxy group, an isopropoxy group anda hydrogen atom.
 4. The compound of claim 1 wherein Y is selected fromthe group consisting of a methyl group, an ethyl group, an n-propylgroup and an isopropyl group.
 5. The compound of claim 1 wherein Q isselected from the group consisting of a substituted or non-substitutedC₃-C₈-cycloalkyl-C₁-C₈-alkyl, substituted or non-substitutedC₃-C₈-cycloalkenyl, substituted or non-substituted C₂-C₈-alkynyl,substituted or non-substituted C₃-C₈-halogenoalkoxy having 1 to 5halogen atoms, substituted or non-substituted C₁-C₈-halogenoalkoxyalkylhaving 1 to 5 halogen atoms, substituted or non-substitutedphenoxyalkyl, substituted or non-substituted C₂-C₈-alkenyloxy,substituted or non-substituted C₂-C₈-halogenoalkenyloxy having 1 to 5halogen atoms, substituted or non-substituted C₃-C₈-alkynyloxy,substituted or non-substituted C₃-C₈-halogenoalkynyloxy having 1 to 5halogen atoms, substituted benzyloxy, substituted or non-substitutedphenoxy, substituted aryl, substituted or non-substituted, saturated orunsaturated 4-, 5-, 6- or 7-membered heterocyclyl comprising up to 4heteroatoms selected from the group consisting of N, O, and S;substituted or non-substituted, saturated or unsaturated 4-, 5-, 6- or7-membered heterocyclyl-[C₁-C₈]-alkyl comprising up to 4 heteroatomsselected from the group consisting of N, O, and S; saturated orunsaturated 4-, 5-, 6- or 7-membered heterocyclyl-[C₃-C₈]-halogenoalkylcomprising up to 4 heteroatoms selected from the group consisting of N,O, and S and having 1 to 5 halogen atoms; substituted or non-substitutedC₅-C₁₂-fused bicycloalkyl, and substituted or non-substitutedC₅-C₁₂-fused bicycloalkenyl.
 6. The compound of claim 5 wherein Q isselected from the group consisting of a substituted or non-substitutedC₃-C₈-cycloalkyl-C₁-C₈-alkyl, substituted or non-substitutedC₃-C₈-cycloalkenyl, substituted or non-substituted C₂-C₈-alkynyl,substituted or non-substituted C₁-C₈-halogenoalkoxy having 1 to 5halogen atoms, substituted or non-substituted phenoxyalkyl, substitutedor non-substituted C₂-C₈-alkenyloxy, substituted or non-substitutedC₃-C₈-alkynyloxy, substituted or non-substitutedC₃-C₈-halogenoalkynyloxy having 1 to 5 halogen atoms, substitutedbenzyloxy, substituted or non-substituted phenoxy, substituted aryl,substituted or non-substituted, saturated or unsaturated 4-, 5-, 6- or7-membered heterocyclyl comprising up to 4 heteroatoms selected from thegroup consisting of N, O, and S; and substituted or non-substituted,saturated or unsaturated 4-, 5-, 6- or 7-memberedheterocyclyl-[C₁-C₈]-alkyl comprising up to 4 heteroatoms selected fromthe group consisting of N, O, and S.
 7. The compound of claim 6 whereinQ is selected from the group consisting of a substituted ornon-substituted C₃-C₈-cycloalkyl-C₁-C₈alkyl, substituted ornon-substituted C₂-C₈-alkynyl, substituted or non-substitutedC₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms, substituted ornon-substituted phenoxyalkyl, substituted or non-substitutedC₂-C₈-alkenyloxy, substituted or non-substituted C₃-C₈-alkynyloxy,substituted aryl, substituted or non-substituted, saturated orunsaturated 4-, 5-, 6- or 7-membered heterocyclyl comprising up to 4heteroatoms selected from the group consisting of N, O, and S; andsubstituted or non-substituted, saturated or unsaturated 4-, 5-, 6- or7-membered heterocyclyl-[C₁-C₈]-alkyl comprising up to 4 heteroatomsselected from the group consisting of N, O, and S.
 8. A fungicidecomposition comprising, as an active ingredient, an effective amount ofthe compound of claim 1 and an agriculturally acceptable support,carrier or filler.
 9. A method for controlling phytopathogenic fungi ofcrops comprising applying an agronomically effective and substantiallynon-phytotoxic quantity of the compound of claim 1 to the soil whereplants grow or are capable of growing, to the leaves and/or the fruit ofplants or to the seeds of plants.
 10. A method for controllingphytopathogenic fungi of crops comprising applying an agronomicallyeffective and substantially-non-phytotoxic quantity of the compositionof claim 8 to the soil where plants grow or are capable of growing, tothe leaves and/or the fruit of plants or to the seeds of plants.